Substituted N-aryl nitrogen-containing heterocyclic compounds

ABSTRACT

The invention relates to novel substituted N-aryl nitrogen-containing heterocyclic compounds of the general formula (I)  
                 
 
     and to the compounds isomeric to the substituted N-aryl nitrogen-containing heterocyclic compounds of the formula (I), of the formulae (Ia) and (Ib)  
                 
 
     in which  
     Q 1 , Q 2 , R 1 , R 2  and Ar have the meanings given in the description, processes for their preparation and their use as herbicides.

[0001] The invention relates to novel substituted N-arylnitrogen-containing heterocyclic compounds, processes for theirpreparation and their use as herbicides.

[0002] It is known that certain N-aryl nitrogen-containing heterocycliccompounds have herbicidal properties (cf. EP 11693, DE 2952685, DE3026739, U.S. Pat. Nos. 4,276,420, and 4,326,878, WO 94/14817). However,the compounds known from the patent applications mentioned have notacquired noteworthy importance.

[0003] The novel substituted N-aryl nitrogen-containing heterocycliccompounds of the general formula (I)

[0004] in which

[0005] Q¹ represents oxygen or sulfur,

[0006] Q² represents oxygen or sulfur,

[0007] R¹ represents hydrogen, cyano or formyl or represents alkyl whichis optionally substituted by halogen, cyano, carboxyl, alkoxy,alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio,alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl,

[0008] R¹ furthermore represents alkenyl or alkinyl, in each caseoptionally substituted by halogen,

[0009] R¹ furthermore represents alkylcarbonyl, alkenylcarbonyl,alkinylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl oralkinyloxycarbonyl, in each case optionally substituted by halogen,

[0010] R¹ furthermore represents cycloalkyl or cycloalkylcarbonyl, ineach case optionally substituted by halogen, cyano or carboxyl,

[0011] R² represents hydrogen, cyano or formyl, or represents alkylwhich is optionally substituted by halogen, cyano, carboxyl, alkoxy,alkenyloxy, alkinyloxy, alkilthio, alkenylthio, alkinylthio,alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl,

[0012] R² furthermore represents alkenyl or alkinyl, in each caseoptionally substituted by halogen,

[0013] R² furthermore represents alkylcarbonyl, alkenylcarbonyl,alkinylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl oralkinyloxycarbonyl, in each case optionally substituted by halogen,

[0014] R² furthermore represents cycloalkyl or cycloalkylcarbonyl, ineach case optionally substituted by halogen, cyano or carboxyl, and

[0015] Ar represents the substituted monocyclic or bicyclic aryl orheteroaryl grouping defined below.

[0016]  in which

[0017] R³ represents hydrogen or halogen,

[0018] R⁴ represents hydrogen or halogen,

[0019] R⁵ represents cyano, carboxyl, chlorocarbonyl, carbamoyl,thiocarbamoyl, hydroxyl or halogen, or represents alkyl, alkoxy oralkoxycarbonyl, in each case optionally substituted by halogen,

[0020] R⁶ represents the following grouping

—A¹—A²—A³

[0021]  in Which

[0022] A¹ represents a single bond, or represents oxygen, sulfur, —SO—,—SO₂—, —CO— or the grouping —N—A⁴—, in which A⁴ represents hydrogen,hydroxyl, alkyl, alkenyl, alkinyl, alkoxy, aryl, alkylcarbonyl,arylcarbonyl, alkylsulfonyl or arylsulfonyl,

[0023] A¹ furthermore represents alkanediyl, alkanediyl, azaalkenediyl,alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, in each caseoptionally substituted by halogen,

[0024] A² represents a single bond, or represents oxygen, sulfur, —SO—,—SO₂—, —CO— or the grouping —N—A⁴—, in which A⁴ represents hydrogen,hydroxyl, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl,

[0025] A² furthermore represents alkanediyl, alkanediyl, azaalkenediyl,alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, in each caseoptionally substituted by halogen,

[0026] A³ represents hydrogen, with the proviso that in this case A¹and/or A² do(es) not represent any single bond,

[0027] A³ furthermore represents hydroxyl, mercapto, amino, cyano,isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo,chloro-sulfonyl or halogen, or represents alkyl, alkoxy, alkylthio,alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonylor dialkoxy(thio)-phosphoryl, in each case optionally substituted byhalogen or alkoxy,

[0028] A³ furthermore represents alkenyl, alkenyloxy, alkenylthio,alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkinyl, alkinyloxy,alkinylthio, alkinylamino or alkinyloxycarbonyl, in each case optionallysubstituted by halogen,

[0029] A³ furthermore represents cycloalkyl, cycloalkyloxy,cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino,cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, in each caseoptionally substituted by halogen cyano, carboxyl, alkyl and/oralkoxy-carbonyl,

[0030] A³ furthermore represents aryl, aryloxy, aralkyl, arylalkoxy,aryloxycarbonyl or arylalkoxycarbonyl, in each case optionallysubstituted by nitro, cyano, carboxyl, halogen alkyl, halogenalkyl,alkyloxy, halogenalkyloxy and/or alkoxy-carbonyl,

[0031] A³ furthermore represents in each case optionally completely orpartly hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl,oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl,pyrimidinyl, triazinyl, pyrazolylalkenyl, furylalkyl, thienylalkyl,oxazolylalkyl, isoxazolylalkyl, thiazolylalkyl, pyridinylalkyl,pyrimidinylalkyl, pyrazolylalkoxy or furylalkyl, or representsperhydropyranylalkoxy or pyridylalkoxy, and

[0032] R⁷ represents hydrogen or halogen,

[0033] or in each case two adjacent radicals—R³ and R⁴, R⁴ and R⁵, R⁵and R⁶ or R⁶ and R⁷—together represent one of the following groupings

[0034] —Q³—CQ⁴—, —Q³—CQ⁴—Q⁵—, —Q³—C(R⁸,R⁹)—Q⁵—, —C(R⁸,R⁹)—CQ⁴—,—C(R⁸,R⁹)—Q³—CQ⁴—, —Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—, —Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—Q⁵—,—C(R⁸,R⁹)—CQ⁴—, —Q³—C(R⁸)═C(R⁸)—, —C(R⁸)═C(R⁸)—CQ⁴—, —Q³—C(R⁸,R⁹)—CQ⁴—,—N(R¹⁰)—C(R⁸,R⁹)—CQ⁴—, —C(R⁸)═N—, —Q³—CQ⁴—C(R⁸,R⁹)—, —Q³—CQ⁴—N(R¹⁰)—,—Q³—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—, —C(R⁸,R⁹)—CQ³—CQ⁴—N(R¹⁰)—,—C(R⁸,R⁹)—C(R⁸,R⁹)—N(R¹⁰)—, —C(R⁸,R⁹) —C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—,—C(R⁸)═C(R⁸)—N(R¹⁰)—, —C(R⁸)═C(R⁸)—CQ⁴—N(R¹⁰)—, —C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—,—N(R¹⁰)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—, —C(R⁸)═N—N(R¹⁰)—,—Q³—C—Q⁴—C(R⁸,R⁹)—N(R¹⁰)—, —Q³—C(R⁸,R⁹)—(R⁸,R⁹)—CQ⁴—N(R¹⁰)—

[0035]  in which

[0036] Q³, Q⁴ and Q⁵ are identical or different and in each caserepresent oxygen or sulfur,

[0037] R⁸ and R⁹ are identical or different and individually representhydrogen, halogen or alkyl or together represent alkanediyl, and

[0038] R¹⁰ represents hydrogen or hydroxyl, or represents alkyl,alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl Which are optionallysubstituted by cyano, halogen, alkoxy, alkyl-carbonyl oralkoxy-carbonyl, or represents alkenyl or alkinyl, in each caseoptionally substituted by halogen, or represents cycloalkyl orcycloalkylalkyl, in each case optionally substituted by halogen oralkyl, or represents alkoxy or alkenyloxy, in each case optionallysubstituted by halogen or represents arylalkyl or arylalkoxy, in eachcase optionally substituted by cyano, halogen, alkyl, halogenoalkyl,alkoxy or halogenoalkoxy,

[0039] have now been found, the already known compounds4-(3,4-dichlorophenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one and4-(4-chloro-3-trifluoromethylphenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one(cf. DE 2952685 and DE 3026739) being excluded by disclaimer.

[0040] The compounds isomeric to the substituted N-arylnitrogen-containing heterocyclic compounds of the formula (I), of theformulae (Ia) and (Ib)

[0041] in which

[0042] Q¹, Q², R¹, R² and Ar have the abovementioned meanings, havefurthermore also been found.

[0043] The novel substituted N-aryl nitrogen-containing heterocycliccompounds of the general formula (I) and, where appropriate, thecompounds of the formulae (Ia) or (Ib) are obtained when

[0044] (a) (thio)semicarbazide derivatives of the general formula (II)

[0045]  in which

[0046] Q¹, Q², R¹, R² and Ar have the abovementioned meanings and

[0047] R represents alkyl.

[0048]  are subjected to a cyclizing condensation reaction, ifappropriate in the presence of a reaction auxiliary and if appropriatein the presence of a diluent, and thereafter, if appropriate,electrophilic or nucleophilic substitution reactions are carried out inthe customary manner in the context of the definition of thesubstituents.

[0049] or when

[0050] (b) aryliminoheterocyclic compounds of the general formula (III)

[0051]  in which

[0052] Q¹, Q², R¹, R² and Ar have the abovementioned meanings, —orcompounds of the formula (Ia) or (Ib)—above—

[0053] are isomerized thermally (“pyrolytically”), if appropriate in thepresence of a reaction auxiliary and if appropriate in the presence of adiluent

[0054] The compounds of the formula (I) can in principle also besynthesized as shown schematically below:

[0055] (c) reaction of aryl iso(thio)cyanates of the formula (IV) withhydrazines of the formula (V) to give aryl(thio)semicarbazides of theformula (VI) and reaction thereof with (thio)phosgene:

[0056] (d) reaction of aryl iso(thio)cyanates of the formula (IV) withS-alkyldithio-carbazates of the formula (VII) and subsequent cyclizingcondensation:

[0057] (e) reaction of N,N-bis-chlorocarbonyl- orN,N-bis-phenoxycarbonyl-arylamines of the formula (VIII)—Y:Cl orOC₆H₅—with hydrazines of the formula (V):

[0058] (f) reaction of arylamines of the formula (IX) withhydrazinedicarboxylic acid esters of the formula (X):

[0059] The compounds of the general formula (I) can also be convertedinto other compounds of the general formula (I) according to the abovedefinition by further customary methods, for example by customary,conversions of carboxylic acid groupings or derivatives thereof (forexample R⁵: COOH→COCl, COOH→COOCH₃, COCl→CONH₂, COOCH₃→CONH₂, CONH₂ →CN,CN→CSNH₂), by alkylation reactions (for example R¹: H→CH₃ or CHF₂) or byoxidation or sulfurization (for example Q¹: O→S or S→O)—cf. also thepreparation examples.

[0060] The novel substituted N-aryl nitrogen-containing heterocycliccompounds of the general formula (I) are distinguished by a potentherbicidal activity.

[0061] In the definitions, the saturated or unsaturated hydrocarbonchains, such as alkyl, alkenyl or alkinyl, are in each casestraight-chain or branched.

[0062] Halogen in general represents fluorine, chlorine, bromine oriodine, preferably fluorine, chlorine or bromine, in particular fluorineor chlorine.

[0063] The invention preferably relates to compounds of the formulae(I), (Ia) and (Ib) in which

[0064] Q¹ represents oxygen or sulfur,

[0065] Q² represents oxygen or sulfur,

[0066] R¹ represents hydrogen, cyano or formyl, or representsC₁-C₆-alkyl, in each case optionally substituted by fluorine, chlorine,cyano, carboxyl, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkinyloxy,C₁-C₄-alkylthio, C₃-C₄-alkenylthio, C₃-C₄-alkinylthio,C₁-C₄-alkoxy-carbonyl, C₃-C₄-alkenyloxy-carbonyl orC₃-C₄-alkinyloxy-carbonyl,

[0067] R¹ furthermore represents C₃-C₆-alkenyl or C₃-C₆-alkinyl, in eachcase optionally substituted by fluorine or chlorine.

[0068] R¹ furthermore represents C₁-C₆-alkyl-carbonyl,C₃-C₆-alkenyl-carbonyl, C₃-C₆-alkinyl-carbonyl, C₁-C₆-alkoxy-carbonyl,C₃-C₆-alkenyloxy-carbonyl or C₃-C₆-alkinyloxy-carbonyl, in each caseoptionally substituted by fluorine or chlorine,

[0069] R¹ furthermore represents C₃-C₆-cycloalkyl orC₃-C₆-cycloalkyl-carbonyl, in each case optionally substituted byfluorine, chlorine, bromine, cyano or carboxyl,

[0070] R² represents hydrogen, cyano or formyl, or representsC₁-C₆-alkyl in each case optionally substituted by fluorine, chlorine,cyano, carboxyl, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkinyloxy,C₁-C₄-alkylthio, C₃-C₄-alkenylthio, C₃-C₄-alkylthio,C₁-C₄-alkoxy-carbonyl, C₃-C₄-alkenyloxy-carbonyl or C₃-C₄-alkinyloxycarbonyl,

[0071] R² furthermore represents C₃-C₆-alkenyl or C₃-C₆-alkinyl, in eachcase optionally substituted by fluorine or chlorine.

[0072] R² furthermore represents C₁-C₆-alkyl-carbonyl, C₃-C₆-alkenylcarbonyl, C₃-C₆-alkylcarbonyl, C₁-C₆-alkoxy carbonyl, C₃-C₆-alkenyloxycarbonyl or C₃-C₆-alkinyloxy-carbonyl, in each case optionallysubstituted by fluorine or chlorine,

[0073] R² furthermore represents C₃-C₆-cycloalkyl orC₃-C₆-cycloalkyl-carbonyl, in each case optionally substituted byfluorine, chlorine, bromine, cyano or carboxyl, and

[0074] Ar represents the substituted monocyclic or bicyclic aryl orheteroaryl grouping defined below

[0075]  in which

[0076] R³ represents hydrogen, fluorine, chlorine or bromine,

[0077] R⁴ represents hydrogen, fluorine, chlorine or bromine,

[0078] R⁵ represents cyano, carboxyl, chlorocarbonyl, carbamoyl,thiocarbamoyl, hydroxyl, fluorine, chlorine, bromine or representsalkyl, alkoxy or alkoxycarbonyl having in each case up to 4 carbon atomsand in each case optionally substituted by fluorine and/or chlorine,

[0079] R⁶ represents the following grouping

—A¹—A²—A³

[0080]  in which

[0081] A¹ represents a single bond, or represents oxygen, sulfur, —SO—,—SO₂—, —CO— or the grouping —N—A⁴—, in which A₄ represents hydrogen,hydroxyl, C₁-C₄-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkinyl, C₁-C₄-alkoxy,phenyl, C₁-C₄-alkyl-carbonyl, phenylcarbonyl, C₁-C₄-alkyl-sulfonyl orphenylsulfonyl,

[0082] A¹ furthermore represents C₁-C₆-alkanediyl, C₂-C₆-alkanediyl,C₂-C₆-azaalkenediyl, C₂-C₆-aeinediyl, C₃-C₆-cycloalkanediyl,C₃-C₆-cycloalkenediyl or phenylene, in each case optionally substitutedby fluorine, chlorine or bromine,

[0083] A² represents a single bond, or represents oxygen, sulfur, —SO—,—SO₂—, —CO— or the grouping —N—A⁴—, in which A⁴ represents hydrogen,hydroxyl, C₁-C₄-alkyl, C₁-C₄-alkoxy, phenyl, C₁-C₄-alkylsulfonyl orphenylsulfonyl,

[0084] A² furthermore represents C₁-C₆-alkanediyl, C₂-C₆-alkanediyl,C₂-C₆-azaalkenediyl, C₂-C₆-alkenyl, C₃-C₆-cycloalkanediyl,C₃-C₆-cycloalkenediyl or phenylene, in each case optionally substitutedby fluorine, chlorine or bromine,

[0085] A³ represents hydrogen with the proviso that in this case A¹and/or A² do(es) not represent a single bond

[0086] A³ furthermore represents hydroxyl, mercapto, amino, cyano,isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo,chlorosulfonyl, fluorine, chlorine or bromine.

[0087] A³ furthermore represents alkyl, alkoxy, alkylthio,alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonylor dialkoxy(thio)phosphoryl having in each case 1 to 6 carbon atoms inthe alkyl groups and in each case optionally substituted by fluorine,chlorine or C₁-C₄-alkoxy,

[0088] A³ furthermore represents alkenyl, alkenyloxy, alkenylamino,alkylidenamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino oralkinyloxycarbonyl having in each case 2 to 6 carbon atoms in thealkenyl, alkylidene or alkinyl groups and in each case optionallysubstituted by fluorine or chlorine,

[0089] A³ furthermore represents cycloalkyl, cycloalkyloxy,cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino,cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl having in each case 3to 6 carbon atoms in the cycloalkyl groups and where appropriate 1 to 4carbon atoms in the alkyl groups and in each case optionally substitutedby fluorine, chlorine, cyano, carboxyl, C₁-C₄-alkyl and/or C₁-C₄-alkoxycarbonyl,

[0090] A³ furthermore represents phenyl, phenyloxy, phenyl-C₁-C₄-alkyl,phenyl-C₁-C₄-alkoxy, phenyloxycarbonyl or phenyl-C₁-C₄-alkoxycarbonyl,in each case optionally substituted by nitro, cyano, carboxyl, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkyloxy,C₁-C₄-halogenalkyloxy and/or C₁-C₄-alkoxy-carbonyl,

[0091] A³ furthermore represents in each case optionally completely orpartly hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl,oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl,pyrimidinyl, triazinyl, pyrazolyl-C₁-C₄-alkyl, furyl-C₁-C₄-alkyl,thienyl-C₁-C₄-alkyl, oxazolyl-C₁-C₄-alkyl, isoxazolyl-C₁-C₄-alkyl,thiazolyl-C₁-C₄-alkyl, pyridinyl-C₁-C₄-alkyl, pyrimidinyl-C₁-C₄-alkyl,pyrazolylmethoxy or furylmethoxy, or represents perhydropyranylmethoxyor pyridylmethoxy, and

[0092] R⁷ represents hydrogen, fluorine or chlorine,

[0093] or in each case two adjacent radicals—R³ and R⁴, R⁴ and R⁵, R⁵and R⁶ or R⁶ and R⁷ —together represent one of the following groupings

[0094] —Q³—CQ⁴—, —Q³—CQ⁴—Q⁵—, —Q³—C(R⁸,R⁹)—Q⁵, —C(R⁸,R⁹)—CQ⁴—,—C(R⁸,R⁹)—Q³—CQ⁴—, —Q—C(R⁸,R⁹)—C(R⁸,R⁹)—, —Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—Q⁵—,—C(R⁸,R⁹)—C(R⁸,R⁹)—CQ⁴—, —Q³—C(R⁸)═C(R⁸)—, —C(R⁸)═C(R⁸)—CQ⁴—,—Q³—C(R⁸,R⁹)—CQ⁴—, —N(R¹⁰)—C(R⁸,R⁹)—CQ⁴—, —C(R⁸)═N—, —Q³—CQ⁴—C(R⁸,R⁹)—,—Q³—CQ⁴—N(R¹⁰)—, —Q³—(R⁸,R⁹)—CQ⁴—N(R¹⁰)—, —C(R⁸,R⁹)—Q³—CQ⁴—N(R¹⁰)—,—C(R⁸,R⁹)—C(R⁸,R⁹)—N(R¹⁰)—, —C(R⁸,R⁹)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—,—C(R⁸)═C(R⁸)—N(R¹⁰)—, C(R⁸)═C(R⁸)—CQ⁴—N(R¹⁰)—, —C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—,N(R¹⁰)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—, —C(R⁸)═N—N(R¹⁰)—, —Q³—CQ⁴—C(R⁸,R⁹)—N(R¹⁰)—,Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)

[0095]  in which

[0096] Q³, Q⁴ and Q⁵ are identical or different and in each caserepresent oxygen or sulfur,

[0097] R⁸ and R⁹ are identical or different and individually representoxygen, fluorine, chlorine, bromine or C₁-C₄-alkyl or together representC₂-C₅-alkanediyl, and

[0098] R¹⁰ represents hydrogen or hydroxyl, or represents alkyl,alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl having in each case 1 to6 carbon atoms in the alkyl groups and in each case optionallysubstituted by cyano, fluorine, chlorine, C₁-C₄-alkoxy, C₁-C₄-alkylcarbonyl or C₁-C₄-alkoxy-carbonyl,

[0099] R¹⁰ furthermore represents alkenyl or alkinyl having in each case2 to 6 carbon atoms and in each case optionally substituted by fluorine,chlorine or bromine,

[0100] R¹⁰ furthermore represents cycloalkyl or cycloalkylalkyl havingin each case 3 to 6 carbon atoms in the cycloalkyl groups and wereappropriate 1 to 3 atoms in the alkyl group and in each case optionallysubstituted by fluorine, chlorine, bromine or C₁-C₄-alkyl,

[0101] R¹⁰ furthermore represents alkoxy or alkenyloxy having in eachcase up to 6 carbon atoms and in each case optionally substituted byfluorine and/or chlorine, and

[0102] R¹⁰ furthermore represents benzyl or benzyloxy, in each caseoptionally substituted by cyano, fluorine, chlorine, C₁-C₄-alkyl,C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy,

[0103] the already known compounds4-(3,4-dichloro-phenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-oneand4-(4-chloro-3-trifluoromethyl-phenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one(cf. DE 2952685 and DE 3026739) being excluded by disclaimer.

[0104] The invention particularly relates to compounds of the formulae(I), (Ia) and (Ib) in which

[0105] Q¹ represents oxygen or sulfur,

[0106] Q² represents oxygen or sulfur,

[0107] R¹ represents hydrogen, cyano or formyl or represents methyl,ethyl, n- or i-propyl or n-, i-, s- or t-butyl, in each case optionallysubstituted by fluorine, chlorine, cyano, carboxyl, methoxy or ethoxy,

[0108] R¹ furthermore represents propenyl, butenyl, propinyl or butinyl,in each case optionally substituted by fluorine or chlorine,

[0109] R¹ furthermore represents acetyl, propionyl, methoxycarbonyl orethoxycarbonyl, in each case optionally substituted by fluorine orchlorine.

[0110] R¹ furthermore represents cyclopropyl which is optionallysubstituted by fluorine or chlorine,

[0111] R²represents hydrogen, cyano or formyl, or represents methyl,ethyl, n- or i-propyl or n-, i-, s- or t-butyl, in each case optionallysubstituted by fluorine, chlorine, cyano, carboxyl, methoxy or ethoxy,

[0112] R² furthermore represents propenyl, butenyl, propinyl or butinyl,in each case optionally substituted by fluorine or chlorine,

[0113] R² furthermore represents acetyl, propionyl, methoxycarbonyl orethoxycarbonyl, in each case optionally substituted by fluorine orchlorine,

[0114] R² furthermore represents cyclopropyl which is optionallysubstituted by fluorine or chlorine, and

[0115] A¹ represents the substituted monocyclic or bicyclic aryl orheteroaryl grouping defined below

[0116]  in which

[0117] P³ represents hydrogen fluorine or chlorine.

[0118] R⁴ represents hydrogen, fluorine or chlorine.

[0119] R⁵ represents cyano thiocarbamoyl, chlorine, bromine methyl,trifluoromethyl. methoxy, difluoromethoxy or trifluoromethoxy,

[0120] R⁶ represents the following grouping

—A¹—A²—A³

[0121] in which

[0122] A¹ represents a single bond, or represents oxygen, sulfur, —SO—,—SO₂—, —CO— or the grouping —N—A⁴—, in which A⁴ represents hydrogen,hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- ori-propoxy, methylsulfonyl or ethylsulfonyl,

[0123] A¹ furthermore represents methylene, ethane-1,1-diyl,ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl,ethene-1,2,-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl,propine-1,2-diyl or propine-1,3-diyl,

[0124] A² represents a single bond, or represents oxygen sulfur, —SO—,—SO₂—, —CO— or the grouping —N—A⁴—, in which A⁴ represents oxygen,hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- ori-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl orphenylsulfonyl,

[0125] A² furthermore represents methylene, ethane-1,1-diyl,ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl,ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl,propine-1,2-diyl or propine-1,3-diyl,

[0126] A³ represents hydrogen, with the proviso that in this case A¹and/or A² do(es) not represent a single bond,

[0127] A³ furthermore represents hydroxyl, amino, cyano, nitro,carboxyl, carbamoyl, sulfo, fluorine, chlorine or bromine.

[0128] A³ furthermore represents methyl, ethyl, n- or i-propyl, n-, i-,s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy,n-, i-, s- or t-butoxy, n-, i- s- or t-pentyloxy, methylthio, ethylthio,n- or i-propylthio, n-, i-, s- or t-butylthio methylsulfinyl,ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n-or i-propylsulfonyl, methylamino. ethylamino, n- or i-propyl amino, n-,i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl,diethoxyphosphoryl, dipropoxyphosphoryl or diisopropoxyphosphoryl, ineach case optionally substituted by fluorine, chlorine, methoxy orethoxy,

[0129] A³ furthermore represents propenyl, butenyl, propenyloxy,butenyloxy, propenylamino, butenylamino, propylidenamino,butylidenamino, propenyloxycarbonyl, butenyloxycarbonyl, propinyl,butinyl, propinyloxy, butinyloxy, propinylamino, butinylamino,propinyloxycarbonyl or butinyloxycarbonyl, in each case optionallysubstituted by fluorine or chlorine,

[0130] A³ furthermore represents cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, cyclopropylmethoxy, cyclo-butylmethoxy,cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidenamino,cyclohexylidenamino, cyclopentyloxy-carbonyl, cyclohexyloxycarbonyl,cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, in each caseoptionally substituted by fluorine, chlorine, cyano, carboxyl, methyl,ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl,

[0131] A³ furthermore represents phenyl, phenyloxy, benzyl, phenylethyl,benzyloxy, phenyloxycarbonyl or benzyloxycarbonyl, in each caseoptionally substituted by nitro, cyano, carboxyl, fluorine, chlorine,bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy,ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy,methoxycarbonyl and/or ethoxycarbonyl,

[0132] A³ furthermore represents in each case optionally completely orpartly hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl,thienyl, oxazolyl, isoxazoly, thiazolyl, isothiazolyl, oxadiazolyl,thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl,furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolylmethyl,thiazolylmethyl,pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy,furylmethoxy or pyridylmethoxy,

[0133] R⁷ represents hydrogen, fluorine or chlorine,

[0134] or in each case two adjacent radicals—R³ and R⁴, R⁴ and R⁵, R⁵and R⁶ or R⁶ and R⁷—together represent one of the following groupings

[0135] —Q³—CQ⁴—, —Q³—CQ⁴—Q⁵—, —Q³—C(R⁸,R⁹)—Q⁵—, —C(R⁸,R⁹)—CQ⁴—,—C(R⁸,R⁹)—Q³—CQ⁴—, —Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—, —Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—Q⁵—,—C(R⁸,R⁹)—C(R⁸,R⁹)—CQ⁴—, —Q³—C(R⁸)═C(R⁸)—, —C(R⁸)═C(R⁸)—CQ⁴—,—Q³—C(R⁸,R⁹)—CQ⁴—, —N(R¹⁰)—C(R⁸,R⁹)—CQ⁴—, —C(R⁸)═N—, —Q³—CQ⁴—C(R⁸,R⁹)—,—Q³—CQ⁴—N(R¹⁰)—, —Q³—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—, —C(R⁸,R⁹)—Q³—CQ⁴—N(R¹⁰)—,—C(R⁸,R⁹)—C(R⁸,R⁹)—N(R¹⁰)—, —C(R⁸,R⁹)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—,—C(R⁸)═C(R⁸)—N(R¹⁰)—, —C(R⁸)═C(R⁸)—CQ⁴—N(R¹⁰)—, —C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—,—N(R¹⁰)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—, —C(R⁸)═N—N(R¹⁰)—,—Q³—CQ⁴—C(R⁸,R⁹)—N(R¹⁰)—, Q³—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—,

[0136]  in wich

[0137] Q³, Q⁴ and Q⁵ are identical or different and in each caserepresent oxygen or sulfur.

[0138] R⁸ and R⁹ are identical or different and individually representhydrogen fluorine, chlorine, methyl or ethyl, or together representethane-1,2-diyl (dimethylene), and

[0139] R¹⁰ represents hydrogen or hydroxyl, or represents methyl, ethyl,n- or i-propyl or n-, i-, s- or t-butyl which are optionally substitutedby cyano, fluorine chlorine, methoxy ethoxy, acetyl, propionyl,methoxycarbonyl or ethoxy-carbonyl,

[0140] R¹⁰ furthermore represents propenyl, butenyl, propinyl orbutinyl, in each case optionally substituted by fluorine, chlorine orbromine,

[0141] R¹⁰ furthermore represents cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, in each case optionally substitute by fluorine,chlorine, bromine, methyl or ethyl,

[0142] R¹⁰ furthermore represents methoxy, ethoxy, n- or i-propoxy, n-,i- or s-butoxy, propenyloxy or butenyloxy, in each case optionallysubstituted by fluorine and/or chlorine, and

[0143] R¹⁰ furthermore represents benzyl or benzyloxy, in each caseoptionally substituted by cyano, fluorine, chlorine, methyl, ethyl,trifluoromethyl, methoxy, ethoxy, difluoromethyl or trifluoromethoxy,

[0144] the already known compounds4-(3,4-dichloro-phenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-oneand4-(4-chloro-3-trifluoromethyl-phenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one(cf. DE 2952685 and DE 3026739) being excluded by disclaimer.

[0145] The above mentioned definitions of radicals given generally or inpreferred ranges apply both to the end products of the formula (I) andalso correspondingly to the staring substances or intermediate productsin each case required for the preparation. These definitions of radicalscan be combined with one another as desired, that is to say also betweenthe stated ranges of preferred compounds.

[0146] Examples of the compounds of the formula (I) according to theinvention are given in the following groups.

Group 1

[0147]

[0148] Ar here has, for example, the meanings listed below:

[0149] 2,4-dichloro-phenyl, 3-chloro-4-fluoro-phenyl,2-chloro-4-cyano-phenyl, 2-fluoro-4-cyano-phenyl, 4,5-difluoro-phenyl,2,4,5-trichloro-phenyl, 2,4-dichloro-5-fluoro-phenyl,2-chloro-4,5-difluoro-phenyl, 4chloro-2,5-di-fluoro-phenyl,5-chloro-2,4-difluoro-phenyl, 2-fluoro-5-chloro-4-cyano-phenyl,2,4,5-trifluoro-phenyl, 2,5-dichloro-4-cyano-phenyl,2-chloro-5-fluoro-4-cyano-phenyl, 2-chloro-4,5-dicyano-phenyl,2-chloro-4-fluoro-5-cyano-phenyl, 2,5-difluoro-4-cyano-phenyl,4-cyano-3-methyl-phenyl, 2-chloro-4-cyano-5-methyl-phenyl,2,4-dichloro-5-methoxy-phenyl, 2,4-dichloro-5-ethoxy-phenyl,2,4-dichloro-5-n-propoxy-phenyl,2,4-dichloro-5-i-propoxy-phenyl,4-chloro-2-fluoro-5-methoxy-phenyl, 4-chloro-2-fluoro-5-ethoxy-phenyl,4-chloro-2-fluoro-5-n-propoxy-phenyl,4-chloro-2-fluoro-5-i-propoxy-phenyl, 2-fluoro-4-cyano-5-methyl-phenyl,2,4-dichloro-5-methyl-phenyl, 2-chloro-4-cyano-5-trifluoromethyl-phenyl,4-fluoro-3-trifluoromethyl-phenyl,2-fluoro-4-cyano-5-trifluoromethyl-phenyl,2-chloro-4-methyl-5-trifluoromethyl-phenyl,2-chloro-5-fluoro-4-methoxy-phenyl, 2-fluoro-4-methoxy-5-methyl-phenyl,2,5-difluoro-4-thicarbamoyl-phenyl,2-chloro-4-fluoro-5-i-propoxy-phenyl, 2-fluoro-4-cyano-5-methoxy-phenyl,2-fluoro-4-cyano-5-i-propoxy-phenyl,2-chloro-4-cyano-5-(2-propinyloxy)-phenyl,2-fluoro-4-cyano-5-(1-methyl-2-propinyloxy)-phenyl,2-fluoro-4-chloro-5-(1-methyl-2-propinyloxy)-phenyl,2-chloro-4-thio-carbamoyl-5-i-propoxy-phenyl,2-fluoro-4-cyano-5-(2-propenyloxy)-phenyl,2-fluoro-4-chloro-5-(2-propenyloxy)-phenyl,2-chloro-4-cyano-5-methyl-sulfonylamino-phenyl,2-fluoro-4-cyano-5-ethylsulfonylamino-phenyl,2-fluoro-4-thiocarbamoyl-5-methylsulfonylamino-phenyl,2-fluoro-4-cyano-5-ethylsulfonylamino-phenyl,2-fluoro-4-cyano-5cyclpropylsulfonylamino-phenyl,2-fluoro-4-cyano-5-i-propylsulfonylamino-phenyl,2-chloro-4-thiocarbamoyl-5-ethylsulfonylamino-phenyl,2-chloro-4-cyano-5-cyanamino-phenyl,2-fluoro-4-cyano-5-(2,2-difluoroethylsulfonylamino)-phenyl,2-fluoro-4-cyano-5-phenyl-sulfonylamino-phenyl,2-fluoro-4-cyano-5-t-butylsulfonylamino-phenyl,2-chloro-4-cyano-5-methoxycarbonyl-phenyl,2-fluoro-4-cyano-5-ethoxycarbonyl-phenyl,2-fluoro-4-chloro-5-ethoxycarbonyl-phenyl,2-fluoro-4-thiocarbamoyl-5-methoxy-carbonyl-phenyl,2-chloro-4-cyano-5-(N-cyclopropyl-ethylsulfonylamino)-phenyl,2-fluoro-cyano-5-(1-methyl-2-propinylthio)-phenyl,2fluoro-4-cyano-5-methylamino-phenyl,2-chloro-4-thiocarbamoyl-5-methoxycarbonylmethyl-phenyl,2-chloro-4-cyano-5-(N-methyl-ethylsulfonylamino)-phenyl,2-fluoro-4-cyano-5-i-propoxycarbonyl-phenyl,2-fluoro-4-chloro-5-i-propoxycarbonyl-phenyl,2-fluoro-4-cyano-5-(bis-ethylsulfonyl-amino)-phenyl,2-fluoro-4-cyano-5-(N-methylsulfonyl-ethylsulfonylamino)-phenyl,2-fluoro-4-cyano-5-(1-methoxycarbonyl-ethoxy)-phenyl,2-fluoro-4-cyano-5-(1-ethoxycarbonyl-ethoxy)-phenyl,2-fluoro-4-chloro-5-(1-methoxycarbonyl-ethoxy)-phenyl,2-fluoro-4-chloro-5-(1-ethoxycarbonyl-ethoxy)-phenyl,2-fluoro-4-cyano-5-cyclopropyloxy-phenyl,2-chloro-4-cyano-5-dimethylamino-phenyl,2-fluoro-4-cyano5-tetrahydrofurylmethoxy-phenyl,4-chloro-2-fluoro-5-tetrahydrofurylmethoxy-phenyl,2-fluoro-4-cyano-5-amino-phenyl,2-fluoro-4-cyano-5-methylaminocarbonyl-phenyl,2-fluoro-4-cyano-5-methysulfonyloxy-phenyl,2-chloro-4-cyano-5-difluoromethoxy-phenyl,2-fluoro-4-chloro-5-methoxycarbonylmethoxy-phenyl,2-fluoro-4-chloro-5-ethoxycarbonyl-methoxy-phenyl,2-fluoro-4-cyano-5-methoxycarbonylmethoxy-phenyl,2-fluoro-4-cyano-5-ethoxycarbonylmethoxy-y-phenyl,4-cyano-3-(1-methyl-2-propinyloxy)-phenyl,2-fluoro-4-cyano-5-dimethyl-aminocarbonyl-phenyl,2-fluoro-4-cyano-5-cyanomethoxy-phenyl,2-fluoro-4-cyano-5-(2-chloro-2-propenyloxy)-phenyl,2-fluoro-4-cyano-5-hydroxy-phenyl, 2-fluoro-4-cyano-5-nitro-phenyl,2-fluoro-4-cyano-5-diethoxyphosphorylamino-phenyl,2-fluoro-4-cyano-5-cholorosulfonyl-phenyl,2-fluoro-4-cyano-5-formylamino-phenyl,2-chloro-4-cyano-5-ethoxycarbonyloxy-phenyl,2-fluoro-4-cyano-5-diethoxy-phosphorylmethoxy-phenyl,4-chioro-2-fluoro-5-diethoxy-phosphorylmethoxy-phenyl,2-fluoro-4-cyano-5-(1-diethoxyphosphoryl-ethoxy)-phenyl,4-chloro-2-fluoro-5(1-diethoxyphosphoryl-ethoxy)-phenyl, 2-chloro-cyano-5-hydroxy-phenyl, 2-fluoro-4-cyano-5-(N,N-diacetyl-amino)-phenyl,2-fluoro-4-cyano-5-acetylamino-phenyl,2-chloro-4-cyano-5-thiocyanato-phenyl,2-fluoro-4-cyano-5-diethylaminooxy-phenyl,2-fluoro-4-cyano-5-tetrahydrofuryloxy-phenyl,2-fluoro-4-cyano-5-ureido-phenyl,2-fluoro-4-cyano-5-dimethoxymethylenamino-phenyl,2-chloro-4-cyano-5-ethoxymethylenamino-phenyl,2-fluoro-4-cyano-5-(2-chloro-ethoxycarbonyl-oxy)-phenyl,2-chloro-4-cyano-5-dimethylaminomethylenamino-phenyl,2-chloro-4-cyano-5-(perhydropyran-4-yloxy)-phenyl,2-fluoro-4-cyano-5-(2-methoxycarbonyl-ethyl)-phenyl,4-chloro-2-fluoro-5-(2-methoxycarbonyl-ethyl)-phenyl,2-chloro-4-cyano-5-(2-carboxy-2-chloro-ethyl)-phenyl,2-fluoro-4-cyano-5-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl,2-fluoro-4-chloro-5-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl,2-fluoro-4-cyano-5-(2-chloro-2-ethoxycarbonyl-ethyl)-phenyl,2-fluoro-4-chloro-5-(2-chloro-2-ethoxycarbonyl-ethyl)-phenyl,2-fluoro-4-cyano-5-(2-bromo-2-methoxycarbonyl-ethyl)-phenyl,2-fluoro-4-chloro-5-(2-bromo-2-methoxycarbonyl-ethyl)-phenyl,2-fluoro-4-cyano-5-(2-bromo-2-ethoxycarbonyl-ethyl)-phenyl,2-fluoro-4-chloro-5-(2-bromo-2-ethoxycarbonyl-ethyl)-phenyl,2-fluoro-4-cayno-5-(2-bromo-2-ethoxycarbonyl-ethyl)-phenyl,2-fluoro-4-cyano-5-(2,3-dibromo-2-methoxycarbonyl-ethyl)-phenyl,2-fluoro-4-chloro-5-(2,3-dibromo-2-methoxycarbonyl-ethyl)-phenyl,2-fluoro-4-cyano-5-(2,3-dibromo-2-ethoxycarbonyl-ethyl)-phenyl,2-fluoro-4-chloro-5-(2,3-dibromo-2-ethoxycarbonyl-ethyl)-phenyl,2-fluoro-4-cyano-5-(2-chloro-2-s-butoxycarbonyl)-phenyl,2-fluoro-4-cyano-5-(2-chloro-2-carbamoyl-ethyl)-phenyl,2-fluoro-4-cyano-5-(2-chloro-2-methoxycarbonyl-1-methyl-ethyl)-phenyl,2-fluoro-4-cyano-5-(1,2-dibromo-2-methoxycarbonyl-ethyl)-phenyl,2-chloro-4-cyano-5-(2-chloro-2-i-propoxy-carbonyl-ethyl)-phenyl,2,4-dichloro-5-(2-methoxy-carbonyl-ethyl)-phenyl,2-fluoro-4-cyano-5-(2-carboxy-2-chloro-ethyl)-phenyl,2-fluoro-4-cyano-5-(2-chloro-2-ethylamino-carbonyl-ethyl)-phenyl,2-fluoro-4-cyano-5-(2-allylaminocarbonyl-2-chloro-ethyl)-phenyl,2-fluoro-4-cyano-5-(2-methoxycarbonyl-ethenyl)-phenyl,2-fluoro-4-chloro-5-(2-methoxycarbonyl-ethenyl)-phenyl,2-fluoro-4-cyano-5-(2-ethoxycarbonyl-ethenyl)-phenyl,2-fluoro-4-chloro-5-(2-ethoxycarbonyl-ethenyl)-phenyl,2-fluoro-4-cyano-5-(2-chloro-2-methylaminocarbonyl-ethyl)-phenyl,2-fluoro-4-cyano-5-(2-chloro-2-ethylaminocarbonyl-ethyl)-phenyl,2-fluoro-4-cyano-5-(2-chloro-2-cyclopropylamino-carbonyl-ethyl)-phenyl,2-fluoro-4-chloro-5-(2-chloro-2-methylaminocarbonyl-ethyl)-phenyl,2-fluoro-4-chloro-5-(2-chloro-2-ethylaminocarbonyl-ethyl)-phenyl,2-fluoro-4-chloro-5-(2-chloro-2-cyclopropylaminocarbonyl-ethyl)-phenyl,2-fluoro-4-cyano-5(2-chloro-2-dimethylaminocarbonyl-ethyl)-phenyl,2-fluoro-4-cyano-5-(2-chloro-2-ethylsulfonylaminocarbonyl-ethyl)-phenyl,2-fluoro-4-chloro-5-(2-chloro-2-ethylsulfonylaminocarbonyl-ethyl)-phenyl,2-fluoro-4-chloro-5-(2-carboxy-ethenyl)-phenyl,2-fluoro-4-thiocarbamoyl-5-(2-ethylaminocarbonyl-ethenyl)-phenyl,2,6-difluoro-4-cyano-5-i-propoxy-phenyl,2-chloro-4-cyano-6-fluoro-3-i-propoxy-phenyl,2-chloro-6-fluoro-3-i-propoxy-4-trifluoromethyl-phenyl,2,6-di-chloro-4-cyano-3-fluoro-phenyl,2-fluoro-4-cyano-5-(1-ethoxycarbonyl-ethyl)-phenyl,2-chloro-4-cyano-5-(1-ethoxycarbonyl-ethyl)-phenyl,2-chloro-4-cyano-5carboxy-phenyl2-fluoro-4-chloro-5-(1-ethoxycarbonyl-ethyl)-phenyl,2-fluoro-4-chloro-5-(1-i-propoxycarbonyl-ethyl)-phenyl,2-fluoro-4-cyano-5-i-butoxy-phenyl), 2-chloro-4-cyano-5-i-butoxy-phenyl,2-chloro-4-cyano-5-(2-methoxy-ethoxy)-phenyl,2-fluoro-4-chloro-5-(2-methoxy-ethoxy)-phenyl,2-fluoro-4-chloro-5-i-butoxy-phenyl,4-hydroxy-4-ethoxycarbonyl-phenyl,2-fluoro-4-cyano-5-i-propoxycarbonyl-phenyl,2-fluoro-4-hydroxy-5-i-propoxycarbonyl-phenyl,2-fluoro-4-cyano-5-(2-oxetanyloxy)-phenyl,2-fluoro-4-cyano-5-(2-oxetanyloxy-carbonylmethoxy)-phenyl,2-fluoro-4-cyano-5-(2-oxetanyloxy)-phenyl,2-fluoro-4-cyano-5-(2-chloro-2-propenyloxy)-phenyl,4-chloro-2-fluoro-5-(2-chloro-2-propenyloxy)-phenyl,2-fluoro-4-chloro-5-methoxycarbonylmethylthio-phenyl,2-fluoro-4-chloro-5-ethoxycarbonylmethylthio-phenyl,2-fluoro-4-cyano-5-methoxycarbonylmethylthio-phenyl,2-fluoro-4-cyano-5-ethoxycarbonylmethylthio-phenyl,2-fluoro-4-chloro-5-(1-methoxycarbonyl-ethylthio)-phenyl,2-fluoro-4-chloro-5(1-ethoxycarbonyl-ethylthio)-phenyl,2-fluoro-4-cyano-5-(1-methoxycarbonyl-ethylthio)-phenyl,2-fluoro-4-cyano-5-(1-ethoxycarbonyl-ethylthio)-phenyl,

[0150] R here represents, for example, hydrogen, hydroxyl, methyl,ethyl, n- or i-propyl, i- or s-butyl, allyl, propargyl, methoxy, ethoxy,n- or i-propoxy, cyanomethyl, carboxymethyl, methoxymethyl,ethoxymethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, acetyl,propionyl, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl orethylsulfonyl.

Group 2

[0151]

[0152] Ar here has, for example, the meanings listed above in Group 1.

Group 3

[0153]

[0154] Ar here has, for example, the meanings listed above in Group 1.

Group 4

[0155]

[0156] Ar here has, for example, the meanings listed above in Group 1.

Group 5

[0157]

[0158] Ar here has, for example, the meanings listed above in Group 1.

Group 6

[0159]

[0160] Ar here has, for example, the meanings listed above in Group 1.

Group 7

[0161]

[0162] Ar here has, for example, the meanings listed above in Group 1.

Group8

[0163]

[0164] Ar here has, for example, the meanings listed above in Group 1.

Group 9

[0165]

[0166] Ar here has, for example, the meanings listed above in Group 1.

Group 10

[0167]

[0168] Ar here has, for example, the meanings listed above in Group 1.

Group 11

[0169]

[0170] Ar here has, for example, the meanings listed above in Group 1.

Group 12

[0171]

[0172] Ar here has, for example, the meanings listed above in Group 1.

Group 13

[0173]

[0174] Ar here has, for example, the meanings listed above in Group 1.

Group 14

[0175]

[0176] Ar here has, for example, the meanings listed above in Group 1.

Group 15

[0177]

[0178] Ar here has, for example, the meanings listed above in Group 1.

Group 16

[0179]

[0180] Ar here has, for example, the meanings listed above in Group 1.

Group 17

[0181]

[0182] Ar here has, for example, the meanings listed above in Group 1.

Group 18

[0183]

[0184] Ar here has, for example, the meanings listed above in Group 1.

Group 19

[0185]

[0186] Ar here has, for example, the meanings listed above in Group 1.

Group 20

[0187]

[0188] Ar here has, for example, the meanings listed above in Group 1.

Group 21

[0189]

[0190] Ar here has, for example, the meanings listed above in Group 1.

Group 22

[0191]

[0192] Ar here has, for example, the meanings listed above in Group 1.

Group 23

[0193]

[0194] Ar here has, for example, the meanings listed above in Group 1.

Group 24

[0195]

[0196] Ar here has, for example, the meanings listed above in Group 1.

Group 25

[0197]

[0198] Ar here has, for example, the meanings listed above in Group 1.

Group 26

[0199]

[0200] Ar here has, for example, the meanings listed above in Group 1.

Group 27

[0201]

[0202] Ar here has, for example, the meanings listed above in Group 1.

Group 28

[0203]

[0204] Ar here has, for example, the meanings listed above in Group 1.

Group 29

[0205]

[0206] Ar here has, for example, the meanings listed above in Group 1.

Group 30

[0207]

[0208] Ar here has, for example, the meanings listed above in Group 1.

Group 31

[0209]

[0210] Ar here has, for example, the meanings listed above in Group 1.

Group 32

[0211]

[0212] Ar here has, for example, the meanings listed above in Group 1.

Group 33

[0213]

[0214] Ar here has, for example, the meanings listed above in Group 1.

Group 34

[0215]

[0216] Ar here has, for example, the meanings listed above in Group 1.

Group 35

[0217]

[0218] Ar here has, for example, the meanings listed above in Group 1.

Group 36

[0219]

[0220] Ar here has, for example, the meanings listed above in Group 1.

Group 37

[0221]

[0222] Ar here has, for example, the meanings listed above in Group 1.

Group 38

[0223]

[0224] Ar here has, for example, the meanings listed above in Group 1.

Group 39

[0225]

[0226] Ar here has, for example, the meanings listed above in Group 1.

Group 40

[0227]

[0228] Ar here has, for example, the meanings listed above in Group 1.

Group 41

[0229]

[0230] Ar here has, for example, the meanings listed above in Group 1.

Group 42

[0231]

[0232] Ar here has, for example, the meanings listed above in Group 1.

Group 43

[0233]

[0234] Ar here has, for example, the meanings listed above in Group 1.

Group 44

[0235]

[0236] Ar here has, for example, the meanings listed above in Group 1.

Group 45

[0237]

[0238] Ar here has, for example, the meanings listed above in Group 1.

Group 46

[0239]

[0240] Ar here has, for example, the meanings listed above in Group 1.

Group 47

[0241]

[0242] Ar here has, for example, the meanings listed above in Group 1.

Group 48

[0243]

[0244] Ar here has, for example, the meanings listed above in Group 1.

Group 49

[0245]

[0246] Ar here has, for example, the meanings listed above in Group 1.

Group 50

[0247]

[0248] Ar here has, for example, the meanings listed above in Group 1.

Group 51

[0249]

[0250] Ar here has, for example, the meanings listed above in Group 1.

Group 52

[0251]

[0252] Ar here has, for example, the meanings listed above in Group 1.

Group 53

[0253]

[0254] Ar here has, for example, the meanings listed above in Group 1.

Group 54

[0255]

[0256] Ar here has, for example the meanings listed above in Group 1.

Group 55

[0257]

[0258] Ar here has, for example, the meanings listed above in Group 1.

Group 56

[0259]

[0260] Ar here has, for example, the meanings listed above in Group 1.

Group 57

[0261]

[0262] Ar here has, for example, the meanings listed above in Group 1.

Group 58

[0263]

[0264] Ar here has, for example, the meanings listed above in Group 1.

Group 59

[0265]

[0266] Ar here has, for example, the meanings listed above in Group 1.

Group 60

[0267]

[0268] Ar here has, for example, the meanings listed above in Group 1.

Group 61

[0269]

[0270] Ar here has, for example, the meanings listed above in Group 1.

Group 62

[0271]

[0272] Ar here has, for example, the meanings listed above in Group 1.

Group 63

[0273]

[0274] Ar here has, for example, the meanings listed above in Group 1.

Group 64

[0275]

[0276] Ar here has, for example, the meanings listed above in Group 1.

Group 65

[0277]

[0278] Ar here has, for example, the meanings listed above in Group 1.

Group 66

[0279]

[0280] Ar here has, for example, the meanings listed above in Group 1.

Group 67

[0281]

[0282] Ar here has, for example, the meanings listed above in Group 1.

Group 68

[0283]

[0284] Ar here has, for example, the meanings listed above in Group 1.

Group 69

[0285]

[0286] Ar here has, for example, the meanings listed above in Group 1.

Group 70

[0287]

[0288] Ar here has, for example, the meanings listed above in Group 1.

Group 71

[0289]

[0290] Ar here has, for example, the meanings listed above in Group 1.

Group 72

[0291]

[0292] Ar here has, for example, the meanings listed above in Group 1.

Group 73

[0293]

[0294] Ar here has, for example, the meanings listed above in Group 1.

Group 74

[0295]

[0296] Ar here has, for example, the meaning listed above in Group 1.

Group 75

[0297]

[0298] Ar here has, for example, the meanings listed above in Group 1.

[0299] If, for example,4-(4-cyano-2,5-difluoro-phenyl)-1-methoxycarbonylthiosemicarbazide isused as the starting substance, the course of the reaction in process(a) according to the invention can be represented by the followingequation:

[0300] If, for example,2-(4-chloro-2-fluoro-5-methoxy-phenylimino)-3,4-dimethyl-3,4-dihydro-5-oxo-1,3,4-thiadiazoleis used as the starting substance, the course of the reaction in process(b) according to the invention can be outlined by the followingequation:

[0301] Formula (II) provides a general definition of the(thio)semicarbazide derivatives to be used as starling substances inprocess (a) according to the invention for the preparation of thecompounds of the general formula (I). In formula (II), Q¹, Q², R¹, R²and Ar preferably or in particular have those meanings which havealready been mentioned above as preferred or as particularly preferredfor Q¹, Q², R¹, R² and Ar in connection with the description of thecompounds of the formula (I); preferably represents alkyl having 1-4carbon atoms, in particular methyl or ethyl.

[0302] The starting substances of the formula (II) are known and/or canbe prepared by known processes (cf. Synthesis 1982, 159-160; DE 1200824,DE 2952685 and DE 3026739).

[0303] The (thio)semicarbazide derivatives of the formula (II) areobtained when

[0304] (α) aryl iso(thio)cyanates of the general formula (IV)

Ar—N═C═Q¹  (IV)

[0305]  in which

[0306] Ar and Q¹ have the abovementioned meanings,

[0307] are reacted with carbazates of the general formula (XI)

RO—CQ²—N(R²)—NH—R¹  (XI)

[0308]  in which

[0309] Q², R¹ and R² have the abovementioned meanings and

[0310] R represents alkyl, and preferably represents C₁-C₆-alkyl, andparticularly preferably represents methyl or ethyl,

[0311] if appropriate in the presence of a diluent, such as, forexample, toluene, at temperatures of between 0° C. and 150° C. (cf. thepreparation examples),

[0312] or when

[0313] (β) arylamines of the general formula (XII)

Ar—NH₂  (XII)

[0314]  in which

[0315] Ar has the abovementioned meaning,

[0316] are reacted with (thio)carbonyl-diimidazole of the formula (XIII)

Im—CQ¹—Im  (XIII)

[0317] in which

[0318] Q¹ has the abovementioned meaning and

[0319] Im represents imidazolyl, and with carbazates of the generalformula (XI)

RO—CQ²—N(R²)—NH—R¹  (XI)

[0320]  in which

[0321] Q², R¹ and R² have the abovementioned meanings and

[0322] R represents alkyl, and preferably represents C₁-C₆-alkyl, andparticularly preferably represents methyl or ethyl,

[0323] if appropriate in the presence of a reaction auxiliary, such as,for example, potassium hydroxide, and if appropriate in the presence ofa diluent, such as, for example, methanol, ethanol and/or water, attemperatures of between 0° C. and 100° C.

[0324] The aryl iso(thio)cyanates of the formula (IV) required asprecursors are known and/or can be prepared by known processes (cf. DE4327743, DE 4335438 and DE 4343451).

[0325] The carbazates of the formula (VIII) furthermore required asprecursors are known organic chemicals.

[0326] Process (a) according to the invention is preferably carried outin the presence of a suitable reaction auxiliary. Possible reactionauxiliaries are all the customary organic or inorganic bases. Theseinclude, for example, alkali metal or alkaline earth metal hydrides,hydroxides, amides, alcoholates, acetates, carbonates orhydrogencarbonates, such as, for example, lithium, sodium, potassium orcalcium hydride, lithium, sodium or potassium amide, sodium or potassiummethylate, sodium or potassium ethylate, sodium or potassium propylate,aluminum isopropylate, sodium or potassiun tert-butylate, sodium orpotassium hydroxide, ammonium hydroxide, sodium, potassium or calciumacetate, ammonium acetate, sodium, potassium, rubidium, cesium,magnesium or calcium carbonate, ammonium carbonate and sodium orpotassium hydrogencarbonate, and basic organic nitrogen compounds, suchas trimethylamine, triethylamine, tripropylamine, tributylamine,ethyl-diisopropylamine, N,N-dimethylcyclohexylamine, dicyclohexylamine,ethyl-dicyclohexylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine,pyridine, 2-methyl-, 3-methyl- and 4-methyl-pyridine, 2,4-dimethyl-,2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine,5-ethyl-2-methyl-pyridine, N-methylpiperidine,N,N-dimethylaminopyridine, diazabicyclooctane, (DABCO),diazabicyclononene (DBN) or diazabicycloundecene (DBU).

[0327] Possible diluents for carrying out process (a) according to theinvention are the customary organic solvents. These include, inparticular, aliphatic, alicyclic or aromatic, optionally halogenatedhydrocarbons, such as, for example, pentane, hexane, heptane, petroleumether, ligroin, benzine, benzene, toluene, xylene, chlorobenzene,dichlorobenzene, cyclohexane, methylcyclohexane, methylene chloride,chloroform or carbon tetrachloride; ethers, such as diethyl ether,diisopropyl ether, t-butyl methyl ether, t-pentyl methyl ether, dioxane,tetrahydrofuran, ethylene glycol dimethyl or diethyl ether or diethyleneglycol dimethyl or diethyl ether, ketones, such as acetone, butanone ormethyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile,butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methyl-pyrrolidone orhexamethylphosphoric acid triamide; esters, such as methyl, ethyl, n- ori-propyl or n-, i- or s-butyl acetate; sulfoxides, such as dimethylsulfoxide; alcohols, such as methanol, ethanol, n- or i-propanol, n-,i-, s- or t-butanol, ethylene glycol monomethyl or monoethyl, ether,diethylene glycol monomethyl ether or diethylene glycol monoethyl ether;and mixtures thereof with water or pure water.

[0328] The reaction temperatures can be varied within a substantialrange when carrying out process (a) according to the invention. Theprocess is in general carried out at temperatures of between 0° C. and+150° C., preferably at temperatures between 10° C. and 120° C.

[0329] Process (a) according to the invention is in general carried outunder normal pressure. However, it is also possible to carry out theprocess under increased or reduced pressure—in general between 0.1 barand 10 bar.

[0330] For carrying out process (a) according to the invention, thestarting substances of formula (II) are in general initially introducedinto the reaction vessel in a suitable diluent and—if appropriate afteraddition of a reaction auxiliary—are stirred at the required temperateuntil the reaction has ended. Working up can be carried out in thecustomary manner (cf. the preparation examples).

[0331] Formula (III) provides a general definition of thearyliminoheterocyclic compounds to be used as starting substances inprocess (b) according to the invention for the preparation of thecompounds of the general formula (I). In formula (III), Q¹, Q², R¹, R²and Ar preferably or in particular have those meanings which havealready been mentioned above as preferred or as particularly preferredfor Q¹, Q², R¹, R² and Ar in connection with the description of thecompounds of the formula (I).

[0332] The starting substances of the formula (III) are not yet knownfrom the literature; however, they are the subject of a priorapplication which has not previously been published (cf. DE 4424787).

[0333] The aryliminoheterocyclic compounds of the formula (III) areobtained when aryl(thio)semicarbazides of the general formula (VI) arereacted with reactive carbonic acid derivatives, such as, for example,phosgene or thiophosgene, if appropriate in the presence of diluents,such as, for example, toluene and/or methylene chloride, at temperaturesof between 0° and 100° C.

[0334] Formulae (Ia) and (Ib) provide general definitions of thecompounds to be used, if appropriate, as starting substances, in process(b) according to the invention for the preparation of the compounds ofthe general formula (I). In formulae (Ia) and (Ib), Q¹, Q², R¹, R² andAr preferably or in particular have those meanings which have alreadybeen mentioned above as preferred or as particularly preferred for Q¹,Q², R¹, R² and Ar in connection with the description of the compounds ofthe formula (I).

[0335] The compounds of the formula (Ia) or (Ib) are obtained whenN-aryl nitrogen-containing heterocyclic compounds of the general formula(I) in which at least one of the groups R¹ or R² represents hydrogen arereacted with alkylating or acylating agents of the formulae (IXa or(IXb)

X—R¹  (XIVa)

X—R²  (XIVb)

[0336] in which

[0337] R¹ and R² have the abovementioned meanings, with the exception ofhydrogen, and

[0338] X represents halogen—preferably chlorine, bromine or iodine—orone of the groupings —O—SO₂—O—R¹ or —O—SO₂—O—R²,

[0339] if appropriate in the presence of a diluent and if appropriate inthe presence of a reaction auxiliary at tempt of between 0° C. and 80°C. (cf. the preparation examples).

[0340] The same diluents and reaction auxiliaries as in process (a)according to the invention are preferably possible here.

[0341] If appropriate, process (b) according to the invention is carriedout in the presence of a reaction auxiliary. The same reactionauxiliaries as in process (a) according to the invention, butfurthermore in addition also alkali metal sulfides, such as, forexample, sodium sulfide or potassium sulfide, are possible here.

[0342] Process (b) according to the invention is preferably carried outusing a diluent. The same diluents as in process (a) according to theinvention are possible here.

[0343] The reaction temperatures can be varied within a substantialrange when carrying out process (b) according to the invention. Theprocess is in general carried out at temperatures of between 0° C. and+250° C., preferably at temperatures of between 20° C. and 150° C.

[0344] Process (b) according to the invention is in general carried outunder normal pressure. However, it is also possible to carry out theprocess under increased or reduced pressure—in general between 0.1 barand 10 bar.

[0345] For carrying out process (b) according to the invention, thestarting substances of the formula (III) or of the formulae (Ia) or(Ib)—are in general initially introduced into the reaction vessel in asuitable diluent and are stirred at the required temperature until thereaction has ended Working up can be carried out in the customarymanner.

[0346] The active compounds according to the invention can be used asdefoliants, desiccants, agents for destroying broad-leaved plants and,especially, as weed-killers. By weeds, in the broadest sense, there areto be understood all plants which grow in locations where they areundesired Whether the substances according to the invention act as totalor selective herbicides depends essentially on the amount used.

[0347] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[0348] Dicotyledon weeds of the genera: Sinapis, Lepidiunm, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver Centaurea, Trifolium, Ranunculus, Taraxacum.

[0349] Dicotyledon cultures of the genera: Gossypium, Glycine, Beta,Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicor, Arachis, Brassica, Lactucae, Cucumis and Cucurbita.

[0350] Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

[0351] Monocotyledon cults of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

[0352] However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

[0353] The compounds are suitable, depending on the concentration, forthe total combating of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for combating weeds in perennialcultures, for example afforestations, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, inlawns, turf and pasture-land, and-for the selective combating of weedsin annual cultures.

[0354] The compounds of the formula (I) according to the invention areparticularly suitable for selectively combating monocotyledon anddicotyledon weeds in monocotyledon cultures both by the pre-emergenceand by the post-emergence method.

[0355] The active compounds can be convened into the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusting agents, pates, soluble powders, granules,suspension-emulsion concentrates, natural and synthetic materialsimpregnated with active compound, and very fine capsules in polymericsubstances.

[0356] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is liquid solventsand/or solid carriers, optionally with the use of surface-active agents,that is emulsifying agents and/or dispersing agents and/or foam-formingagents.

[0357] In the case of the use of water as an extender, organic solventscm, for example, also be used as auxiliary solvents. As liquid solvents,there are suitable in the main: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol as well as their ethers and esters, ketones, suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulfoxide, as well as water.

[0358] As solid carriers there are suitable: for example ammonium saltsand ground natural minerals, such as kaolins, clays, talc, chalk,quartz, attapulgite, montmorillonite or diatomaceous earth, and groundsynthetic minerals, such as highly disperse silica, alumina andsilicates, as solid carriers for granules there are suitable: forexample crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, as well as synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks; as emulsifyingand/or foam-forming agents there are suitable: for example non-ionic andanionic emulsifiers, such as polyoxyethylene fatty acid esters,polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycolethers, alkylsulfonates, alkyl sulfates, arylsulfonates as well asalbumen hydrolysis products; as dispersing agents there are suitable:for example lignin-sulfite waste liquors and methylcellulose.

[0359] Adhesives such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latexes, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Further additives can bemineral and vegetable oils.

[0360] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organicdyestuffs such as alizarin dyestuffs, azo dyestuff and metalphthalocyanine dyestuffs, and trace nutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0361] The formulations in general contain between 0.1 and 95 percent byweight of active compound, preferably between 0.5 and 90%.

[0362] For controlling weeds, the active compounds according to theinvention, as such or in the form of their formulations, can also beused as mixture with known herbicides, finished formulations or tankmixes being possible.

[0363] Suitable herbicides for the mixtures are known herbicides, forexample anilides such as, for example, diflufenican and propanil;arylcarboxylic acids such as, for example, dichloropicolinic acid,dicamba and picloram; aryloxyalkanoic acids such as, for example, 2,4 D,2,4 DB, 2,4 DP, fluroxypyr, MCPA, MCPP and triclopyr;aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl,fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl andquizalofop-ethyl; azinones such as, for example, chloridazon andnorflurazon; carbamates such as, for example, chlorpropham, desmediphamphenmedipham and propham; chloroacetanilides such as, for example,alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachiorand propachlor, dinitroanilines such as, for example, oryzalin,pendimethalin and trifluralin; diphenyl ethers such as, for example,acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen andoxyfluorfen; ureas such as, for example, chlortoluron, diuron,fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylaminessuch as, for example, alloxydim, clethodim, cycloxydim sethoxydim andtralkoxydim; imidazolinones such as, for example, imazethapyr,imazamethabenz, imazapyr and imazaquin; nitriles such as, for example,bromoxynil, dichlobenil and ioxynil; oxyacetamides such as, for example,mefenacet; sulfonylureas such as, for example, amidosulfuron,bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosufuron,metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl,thifensulfuron-methyl and tribenuron-methyl; thiocarbamates such as, forexample, butylate, cycloate, di-allate, EPTC, esprocarb, molinate,prosulfocarb, thiobencarb and tri-allate; triazines such as, forexample, atrazine, cyanazine, simazine, simetryne, terbutryne andterbutylazine; triazinones such as, for example, hexazinone, metamitronand metribuzin; others such as, for example, aminotriazole, benfuresate,bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr,ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben,pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

[0364] A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellants, plant nutrientsand agents for improving soil structure is also possible.

[0365] The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

[0366] The active compounds according to the invention can be appliedeither before or after emergence of the plants. They can also beincorporated into the soil before sowing.

[0367] The amount of active compound used can vary within a substantialrange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

[0368] The preparation and use of the active compounds according to theinvention can be seen from the following examples.

PREPARATION EXAMPLES Example 1

[0369]

[0370] 20.2 g (75 mmol) of4-(4-cyano-2,5-difluoro-phenyl)-1-ethoxycarbonyl-semicarbazide arestirred in 50 ml of 25% strength aqueous potassium hydroxide solution at80° C. for 2 hours. After the mixture has been cooled to 20° C., it isbrought to pH=4 with concentrated hydrochloric acid and the productobtained as crystals is isolated by filtration.

[0371] 16.0 g (90% of theory) of4-(4-carboxy-2,5-difluorophenyl)-1,2,4-triazoline-2,5-dione of meltingpoint >250° C. are obtained.

Example 2

[0372]

[0373] A mixture of 3.90 g (10 mmol) of4-(4-cyano-2-fluoro-5-methylsulfonylaminophenyl)-2-methyl-1-ethoxycarbonyl-thiosemicarbazide,8.10g (80 mmol) of triethylamine and 100 ml of acetonitrile is stirred atthe reflux temperature for 12 hours. The solvent is removed in vacuo,the residue is stirred with water, the mixture is acidified withconcentrated hydrochloric acid and the product obtained as crystals isisolated by filtration.

[0374] 1.20 g (35% of theory) of4-cyano-2-fluoro-5-methylsulfonylaminophenyl)-1-methyl-5-thioxo-1,2,4-triazolin-3-oneof melting point >250° C. are obtained.

Example 3

[0375]

[0376] A mixture of 5.2 g (15 mmol) of4-(4-chloro-2-fluoro-5-i-propoxycarbonyl-phenyl)-1-methyl-5-thioxo-1,2,4-triazolin-3-one,5.2 g (37.5 mmol) of potassium carbonate and 50 ml of acetonitrile isstirred at 60° C. for 60 minutes; Frigen (CHClF₂) is then passed in at60° C. for 6 hours. The mixture is subsequently concentrated underreduced pressure, the residue is taken up in water, the mixture isacidified with concentrated hydrochloric acid and exited with methylenechloride, and the organic phase is dried over sodium sulfate andfiltered The filtrate is concentrated and the crude product obtained inthe residue is purified by column chromatography (silica gel,hexane/ethyl acetate, Vol.: 7:1).

[0377] 0.7 g (12% of theory) of4-(4-chloro-2-fluoro-5-i-propoxycarbonyl-phenyl)1-methyl-2-difluoromethyl-5-thioxo-1,2,4-triazolin-3-oneof melting point 51° C. is obtained.

Example 4

[0378]

[0379] A mixture of 7.6 g (23 mmol) of2-(7-fluoro-3,4-dihydro-3-oxo-4-propargyl-(2H)-1,4-bezoxazin-6-yl-imino-3-methyl-3,4-dihydro-5-oxo-(4H)-1,3,4-thiadiazoleand 20 ml of dimethyl sulfoxide is heated at 50° C. for 2 hours, at 70°C. for a further 2 hours and at 80° C. for a further 2 hours. It is thenconcentrated under reduced pressure, the residue is stirred with waterand the product obtained as crystals is isolated by filtration.

[0380] 6.6 g (85% of theory) of4-(7-fluoro-3,4-dihydro-3-oxo-4-propargyl-(2H)-1,4-benzoxazin-6-yl)-1-methyl-5-thioxo-1,2,4-triazolin-3-oneof melting point 190° C. are obtained.

[0381] The compounds of the formula (I) listed in the following Table 1,for example, can also be prepared analogously to Examples 1 to 4 and inaccordance with the general description of the preparation processesaccording to the invention. TABLE 1 Examples of the compounds of theformula (I) (I)

Example Physical No. Q¹ Q² R¹ R² Ar data 5 O O H CH₃

M.p.: 234° C. 6 S O CH₃ H

M.p.: 224° C. 7 S O CH₃ CHO

M.p.: 95° C. 8 O S H CH₃

M.p.: 172° C. 9 S O CH₃ CHF₂

M.p.: 183° C. 10 S O CH₃ CH₃

M.p.: 118° C. 11 S O CH₃ H

M.p.: 139° C. 12 S O CH₃ CH₃

M.p.: 227° C. 13 S S CH₃ CH₃

M.p.: 175° C. 14 S O CH₃ CHF₂

M.p.: 122° C. 15 S O CH₃ CHF₂

M.p.: 64° C. 16 S S CH₃ CH₃

M.p.: 155° C. 17 S S CH₃ CH₃

M.p.: 70° C. 18 S S CH₃ CH₃

M.p.: 198° C. 19 S S CH₃ CH₃

20 S S C₂H₅ C₂H₅

M.p.: 120° C. 21 S S CH₃ CH₃

M.p.: 228° C. 22 S S CH₃ CH₃

M.p.: 146° C. 23 S S C₂H₅ C₂H₅

M.p.: 142° C. 24 S S CH₃ CH₃

M.p.: 192° C. 25 S S C₂H₅ C₂H₅

M.p.: 149° C. 26 S S C₂H₅ C₂H₅

M.p.: 195° C. 27 S S C₂H₅ C₂H₅

M.p.: 148° C. 28 S S C₂H₅ C₂H₅

M.p.: 133° C. 29 S S C₂H₅ C₂H₅

30 S S CH₃ CH₃

31 S S C₂H₅ C₂H₅

M.p.: 197° C. 32 S S CH₃ CH₃

M.p.: 229° C. 33 S S CH₃ CH₃

M.p.: 174° C. 34 S S C₂H₅ C₂H₅

M.p.: 103° C. 35 S S CH₃ CH₃

M.p.: 259° C. 36 S S C₂H₅ C₂H₅

M.p.: 248° C. 37 S S CH₃ CH₃

M.p.: 251° C. 38 O S H CH₃

M.p.: 201° C. 39 O S CHO CH₃

M.p.: 75° C. 40 O O CHF₂ CH₃

M.p.: 70° C. 41 O S CH₃ CH₃

M.p.: 157° C. 42 O S CH₃ CH₃

M.p.: 250° C. 43 O S CHF₂ CH₃

M.p.: 127° C. 44 O S CH₃ CH₃

M.p.: 58° C. 45 O S CH₃ CH₃

M.p.: 138° C. 46 O S CH₃ CH₃

M.p.: 236° C. 47 O S

CH₃

M.p.: 122° C. 48 O S

CH₃

49 O S —CH₂CF₃ CH₃

M.p.: 135° C. 50 O S

CH₃

M.p.: 42° C. 51 O S CH₃ CH₃

M.p.: 163° C. 52 O S CHF₂ CH₃

M.p.: 176° C. 53 O S CH₃ CH₃

M.p.: 150° C. 54 O S H CH₃

M.p.: 67° C. 55 O S H H

M.p.: 250° C. 56 O S H CH₃

57 O O

n_(d) ²⁰ = 1.5442 58 O O

n_(d) ²⁰ = 1.5349 59 O O

CH₃

n_(d) ²⁰ = 1.5600 60 O O

61 O O H CH₃

M.p.: 215° C. 62 O O H CH₃

M.p.: 250° C. 63 O O H CH₃

M.p.: 156° C. 64 O O H CH₃

¹H-NMR (CDCl₃): 3.25, 4.40-4.46, 7.22-7.24 ppm 65 O S H CH₃

M.p.: 210° C. 66 O O H CH₃

M.p.: 163° C. 67 O S H CH₃

M.p.: 143° C. 68 O S H CH₃

M.p.: 158° C. 69 O S H CH₃

M.p.: 75° C. 70 O S CH₃ CH₃

¹H-NMR (CDCl₃): 3.45, 3.73, 7.30-7.40 ppm 71 O S CH₃ CH₃

M.p.: 146° C. 72 O S CH₃ CH₃

M.p.: 208° C. 73 O S CH₃ CH₃

M.p.: 195° C. 74 O O H CH₃

(amorphous) 75 O O H H

M.p.: 150° C. 76 O O CH₃ CH₃

M.p.: 101° C. 77 O S

CH₃

M.p.: 172° C. 78 O S

CH₃

M.p.: 199° C. 79 O S H CH₃

amorphous 80 S S CH₃ CH₃

M.p.: 160° C. 81 O S H CH₃

amorphous 82 O S CHF₂ CH₃

M.p.: 99° C. 83 O S CH₃ CH₃

84 S S CH₃ CH₃

M.p.: 131° C. 85 O S CHF₂ CH₃

86 O S C₂H₅ CH₃

[0382] The compound listed as Example 13 in Table 1 can be prepared, forexample, as follows:

[0383] A mixture of 1.0 g (0.3 mmol) of2-(4-cyano-2-fluoro-4-i-propoxy-phenylimino)-3,4-dihydro-3,4-methyl-5-thioxo(4H)-1,3,4-thiadiazole,0.1 g (0.1 mmol) of sodium sulfide and 20 ml of ethanol is heated underreflux for about 20 hours. It is then concentrated, the residue is takenup in methylene chloride and the mixture is washed with water, driedwith sodium sulfate and filtered The filtrate is concentrated, theresidue is digested with diethyl ether and the product obtained ascrystals is isolated by filtration.

[0384] 0.25 g (25% of theory) of4-(4-cyano-2-fluoro-5-i-propoxy-phenyl)1,2-dimethyl-1,2,4-triazoline-2,5-dithioneof melting point 175° C. is obtained.

[0385] The compound listed as Example 21 in Table 1 can be prepared, forexample, as follows:

[0386] Hydrogen sulfide is passed into a mixture of 0.9 g (2.6 mmol) of4-(4-cyano-2-fluoro-5-i-propoxy-phenyl)-1,2-dimethyl-1,2,4-triazoline-2,5-dithione,2 ml (14 mmol) of triethylamine and 20 ml of pyridine at 90° C. for 9hours. After the mixture has been cooled, the solvent is stripped off ona rotary evaporator and the residue is stirred with 2 normalhydrochloric acid. The crude product is filtered off with suction,washed with water, dried and purified by column chromatography (mobilephase: hexane/ethyl acetate 4:1).

[0387] 0.42 g (43% of theory) of4-(2-fluoro-5-i-propoxy-thiocarbamoylphenyl)-1,2-dimethyl-1,2,4-triazoline-2,5-dithioneof melting point 228° C. is obtained.

[0388] The compound listed as Example 46 in Table 1 can be prepared, forexample, as follows:

[0389] A solution of 2.1 g (6 mmol) of4-7-fluoro-3,4-dihydro-3-oxo-4-propargyl-(2H)-1,4-benzoxazin-6-yl)-1-methyl-5-methylthio-1,2,4-triazolin-3-onein 20 ml of dimethylformamide is heated under reflux for 16 hours. It isthen concentrated under a water pump vacuum and the residue is purifiedby column chromatography.

[0390] 0.9 g (43% of theory) of4-(7-fluoro-3,4-dihydro-3-oxo-4-propargyl-(2H)-1,4-benzoxazin-6-yl)-1,2-dimethyl-5-thioxo-1,2,4-triazolin-3-oneof melting point 236° C. is obtained.

[0391] The compound listed as Example 61 in Table 1 can be prepared, forexample, as follows:

[0392] 44.7 g (0.15 mol) of4-(4-cyano-2,5-difluoro-phenyl)-1-ethoxycarbonyl-2-methyl-semicarbazideare stirred in 200 ml of 4 molar aqueous potassium hydroxide solution at80° C. for 30 minutes. After the mixture has been cooled to 20° C., itis brought to pH=4 with concentrated hydrochloric acid and the productobtained as crystals is isolated by filtration.

[0393] 36 g (95% of theory) of4-(4-carboxy-2,5-difluoro-phenyl)-1-methyl-1,2,4-triazoline-3,5-dione ofmelting point 215° C. are obtained.

[0394] The compound listed as Example 62 in Table 1 can be prepared, forexample, as follows:

[0395] 27.1 g (0.1 mol) of4-(4-carboxy-2,5-difluoro-phenyl)-1-methyl-1,2,4-triazole-3,5-dione areheated to 80° C. in 200 ml of toluene, 14.3 g (0.12 mol) of thionylchloride are added dropwise at this tense in the course of 30 minutes,and the mixture is heated to the reflux temperature and stirred forabout 2 hours until the evolution of gas has ended. After the mixturehas been cooled to 20° C., the product obtained as crystals is isolatedby filtration.

[0396] 7.2 g (25% of theory) of4-(4-chlorocarbonyl-2,5-difluoro-phenyl)-1-methyl-1,2,4-triazole-3,5-dioneof melting point >250° C. are obtained.

[0397] The compound listed as Example 63 in Table 1 can be prepared, forexample, as follows:

[0398] 6.5 g (0.024 mol) of4-(4-carboxy-2,5-difluoro-phenyl)-1-methyl-1,2,4-triazole-3,5-dione arestirred at the reflux temperature with 200 ml of methanol and two dropsof sulfuric acid for 8 hours. After the mixture has been cooled to 200°C., it is concentrated under a water pump vacuum the residue isdissolved in methylene chloride, the solution is washed with water andthe organic phase is dried over sodium sulfate and freed thoroughly fromthe solvent under a water pump vacuum.

[0399] 4.2 g (62% of theory) of4-(4-methoxycarbonyl-2,5-difluoro-phenyl)-1-methyl-1,2,4-triazole-3,5-dioneof melting point 156° C. are obtained

[0400] The compound listed as Example 69 in Table 1 can be prepared, forexample, as follows:

[0401] 29.3 g (0.096 mol) of4-(4-chloro-2-fluoro-phenyl)-2-methyl-1-ethoxycarbonyl-thiosemicarbazideare stirred at the reflux temperature in 400 ml of acetonitrile with 78g (0.77 mol) of triethylamine for 8 hours and, after the minute has beencooled, it is concentrated under a water pump vacuum. Water is added tothe residue, the mixture is brought to pH=4 with concentratedhydrochloric acid and extracted with methylene chloride, and the organicphase is separated off, dried over sodium sulfate and concentrated undera water pump vacuum

[0402] 22 g (88% of theory) of4-(4-chloro-2-fluoro-phenyl)-1-methyl-5-thioxo-1,2,4-triazol-3-one ofmelting point 75° C. are obtained.

[0403] The compound listed as Example 70 in Table 1 can be prepared, forexample, as follows:

[0404] 7.1 g (0.026 mol) of the meso ionic compound according to Example(Ia-5)—below—are stirred under reflux in 100 ml of dimethylformamide for18 hours and, after the mixture has been cooled, it is concentratedunder a water pump vacuum.

[0405] 5.9 g (83% of theory) of4-(4-chloro-2-fluorophenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazol-3-oneare obtained.

[0406]¹H-NMR (CDCl₃): 3.45; 3.73; 7.30-7.40 ppm.

[0407] The compound listed as Example 71 in Table 1 can be prepared forexample, as follows:

[0408] 4.65 g (0.017 mol) of4-(4-chloro-2-fluoro-phenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazol-3-oneare initially introduced into the reaction vessel in 30 ml ofconcentrated sulfuric acid, and 3 ml of 98% strength nitric acid areadded dropwise at 0° C. The mixture is subsequently stirred at roomtemperate for 8 hours and stirred with ice water and the product whichhas precipitated out is filtered off.

[0409] 2.9 g (54% of theory) of4-(4-chloro-2-fluoro-5-nitro-phenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazol-3-oneof melting point 146° C. are obtained.

[0410] The compound listed as Example 72 in Table 1 can be prepared, forexample, as follows:

[0411] 2.6 g (0.008 mol) of4-(4-chloro-2-fluoro-5-nitro-phenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazol-3-oneare initially introduced into the reaction vessel in 20 ml of aceticacid with 10 ml of water and 10 ml of ethyl acetate, and 4.6 g (0.0082mol) of iron powder are added in portions, the temple being kept atmaximum of 45° C. using an ice-bath. When the addition has ended, the mis subsequently stirred at 23° C. for 2 hours and filtered with suctionand. the residue is washed with water. The filtrate is extracted withethyl acetate and the organic phase is washed with sodiumhydrogencarbonate solution, dried over sodium sulfate and concentratedunder a water pump vacuum.

[0412] 1.5 g (65% of theory) of4-(4-chloro-2-fluoro-5-amino-phenyl-1,2-dimethyl-5-thioxo-1,2,4-triazol-3-oneof melting point 208° C. are obtained.

[0413] The compound listed as Example 73 in Table 1 can be prepared, forexample, as follows:

[0414] 1.8 g (0.018 mol) of triethylamine and then 2.3 g (0.018 mol) ofethanesulfonyl chloride are added to 1.3 g (0.0045 mol) of4-(4-chloro-2-fluoro-5-amino-phenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazol-3-onein 50 ml of methylene chloride at −10° C., the mixture is stirred atroom temperature for 3 hours, water is added and the organic phase isseparated off, dried over sodium sulfate and concentrated under a waterpump vacuum.

[0415] 2.0 g (94% of theory) of4-[4-chloro-2-fluoro-5-diethylsulfonyl)-amino-phenyl]-1,2-dimethyl-5-thioxo-1,2,4-triazol-3-oneof melting point 195° C. (decomposition) are obtained.

Compounds of the Formulae (Ia) or (Ib) Example (Ia-1)

[0416]

[0417] A mixture of 4.2 g (12 mmol) of4-(4-chloro-2-fluoro-5-i-propoxycarbonyl-phenyl)-1-methyl-5-thioxo-1,2,4-triazolin-3-one,3.5 g (25 mmol) of potassium carbonate, 2.2 g (15 mmol) of methyl iodideand 60 ml of acetonitrile is stirred at 40° C. for 12 hours. It is thenconcentrated, the residue is taken up in water, the mixture is acidifiedwith concentrated hydrochloric acid and extracted with methylenechloride and the organic phase is dried with sodium sulfate andfiltered. The filtrate is concentrated and the crude product obtained asthe residue is purified by column chromatography (silica gel, methylenechloride/methanol, volume: 40:1).

[0418] 1.0 g (24% of theory) of the compound of the structural formulagiven above of melting point 159° C. is obtained.

[0419] The compounds of the formula (Ia) listed in the following Table2, for example, can also be prepared analogously.

TABLE 2 Examples of the compounds of the formula (Ia) Ex- am- plePhysical No. Q¹ Q² R¹ R² Ar data Ia-2 S O CH₃ CH₃

M.p.: 237° C. Ia-3 S O CH₃ CH₃

M.p.: 168° C. Ia-4 S O CH₃ CH₃

M.p.: 185° C. Ia-5 S O CH₃ CH₃

M.p.: 182° C.

[0420] The compound listed as Example (Ia-5) in Table 2 can be prepared,for example, as follows

[0421] 20.7 g(0.08 mol) of4-(4-chloro-2-fluoro-phenyl)-1-methyl-5-thioxo-1,2,4-triazol-3-one areinitially introduced into the reaction vessel with 150 ml of dimethylsulfoxide and 22 g (0.16 mol) of potassium carbonate, 23 g (0.16 mol) ofmethyl iodide are then added dropwise at 0° C. in the course of 30minutes. The mixture is subsequently. stirred at 23° C. for 4 hours andthen concentrated. The residue is stirred with water, the mixture isacidified with concentrated hydrochloric acid and extracted withmethylene chloride, and the organic phase is dried over sodium sulfateand concentrated under a water pump vacuum. After the residue has beenstirred with isopropanol, the product obtained as crystals is isolatedby filtration.

[0422] 7.8 g (36% of theory) of the mesoionic compound of the structuregiven above are obtained.

Starting Substances of the Formula (II) Example (II-1)

[0423]

[0424] 18.0 g (0.10 mol) of 4-cyano-2,5-difluoro-phenyl isocyanate areadded to a solution of 10.4 g (0.10 mol) of ethyl carbazate in 100 ml oftoluene at 10° C. and the mixture is stirred at 20° C. for 2 hours andthen at the reflux temperature for a further 2 hours. The productobtained as crystals after cooling is isolated by filtration.

[0425] 24.2 g (90% of theory) of4-(4-cyano-2,5-difluoro-phenyl)-1-ethoxy-carbonyl-semicarbazide ofmelting point 245° C. are obtained.

Example (II-2)

[0426]

[0427] 18.8 g (0.1 mol) of 4-chloro-2-fluoro-phenyl isothiocyanate arestirred at the reflux temperature in 200 ml of acetonitrile with 11.8 g(0.1 mol) of 2-methyl-1-ethoxy-carbonyl-hydrazine and 9.24 g (0.11 mol)of sodium hydrogencarbonate for 8 hours. After the mixture has beencooled, it is concentrated under a water pump vacuum, the residue isstirred with water, the mixture is extracted with methylene chloride andthe organic phase is separated of; dried over sodium sulfate andconcentrated under a water pump vacuum.

[0428] 29 g (95% of theory) of4-(4-chloro-2-fluoro-phenyl)-2-methyl-1-ethoxy-carbonyl-thiosemicarbazideof melting point 151° C. are obtained.

Starting Substances of the Formula (III) Example (III-1)

[0429]

[0430] 6 g (12 mmol) of a 20% strength solution of phosgene in tolueneare added to a suspension of 3.1 g (10 mmol) of2-methyl-4-(7-fluoro-3,4-dihydro-3-oxo-4-propargyl-(2H)-1,4-benzoxazin-6-yl)-thiosemicarbazidein 50 ml of methylene chloride at about 20° C. The reaction mixture isheated at 40° C. for about 15 hours, the solvent is removed in vacuo andthe residue is taken up in water. The mixture is neutralized with sodiumbicarbonate solution and the solid is filtered off, washed with waterand dried in vacuo at 40-50° C.

[0431] 2.8 g (84% of theory) of2-(7-fluoro-3,4-dihydro-3-oxo-4-propargyl-(2H)-1,4-benzoxazin-6-yl-imino)-3-methyl-3,4-dihydro-5-oxo-(4H)-1,3,4-thiadiazoleare obtained.

[0432] Melting point: 214° C.

Example (III-2)

[0433]

[0434] 0.66 g (5.7 mmol) of thiophosgene is added to a solution of 1.7 g(5.7 mmol) of4-(4-cyano-2-fluoro-5-i-propoxy-phenyl)-1,2-dimethylthiosemicarbazide in30 ml of dry methylene chloride. The reaction is slightly exothermic.The reaction mixture is stirred at the reflux temperature for 4 hours,the solvent is removed in vacuo and the residue is stirred withsaturated sodium carbonate solution. The solid which forms is filteredoff washed with water and pressed off on clay.

[0435] 1.5 g (78% of theory) of2-(4-cyano-2-fluoro-5-i-propoxy-phenylimino)-3,4-dimethyl-5-thio-1,3,4-thiadiazoleof melting point 117° are obtained.

Starting Substances of the Formula (IV) Example (IV-1)

[0436]

[0437] 129 g (1.12 mol) of thiophosgene are added to 81 g (0.56 mol) of4-chloro-2-fluoro-aniline in 500 ml of chlorobenzene at 80° C. to 90° C.in the course of 1 hour and the sure is then stirred at the refluxtemperature for 2 hours until the evolution of gas has ended The clearsolution is concentrated to dryness under a water pump vacuum.

[0438] 102 g (97% of theory) of 4-chloro-2-fluoro-phenyl isothiocyanateare obtained

[0439]¹H-NMR (CDCl₃): 7.10-7.20 ppm; GC-MS: (M=187) 98.4%.

[0440] Use examples:

[0441] Example A

[0442] Pre-emergence test

[0443] Solvent: 5 parts by weight of acetone

[0444] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0445] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0446] Seeds of the test plants are sown in normal soil and, after 24hours, watered with the preparation of the active compound. It isexpedient to keep constant the amount of water per unit area. Theconcentration of the active compound in the preparation is of noimportance, only the amount of active compound applied per unit areabeing decisive. After three weeks, the degree of damage to the plants israted in % damage in comparison to the development of the untreatedcontrol, The figures denote:

[0447] 0%=no action (like untreated control)

[0448] 100%=total destruction

[0449] In this test, for example, the compounds according to preparationexamples 3, 9, 10, 12, 13, 14 and 15, when applied in amounts of 60g/ha, show in some cases a good tolerability toward crop plants, suchas, for example, barley and corn (10-70%) and a very potent actionagainst weeds, such as Alopecurus (90-100%), Cynodon (95-100%), Setaria(70-100%), Amaranthus (90-100%), Chenopodium (100%), Matricaria(95-100%), Polygonum (80-100%), Portulaca (95-100%) and Viola (90-100%).

[0450] Example B

[0451] Post-emergence test

[0452] Solvent: 5 parts by weight of acetone

[0453] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0454] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0455] Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area After threeweeks, the degree of damage to the plants is rated in % damage incomparison to the development of the untreated control, The figuresdenote:

[0456] 0%=no action (like untreated control)

[0457] 100%=total destruction

[0458] In this test, for example, the compounds according to preparationexamples 3, 4, 9, 10, 12, 13, 14 and 15 and Ia-1 and Ia-2, when appliedin amounts of between 15 and 250 g/ha, show a potent action againstweeds, such as Amaranthus (60-100 %), Chenopodium (90-100%), Datura(80-100%), Galium (90-100%) and Veronica (50-100%).

1. A substituted N-aryl nitrogen-containing heterocyclic compound of thegeneral formula (I)

in which Q¹ represents oxygen or sulfur, Q² represents oxygen or sulfur,R¹ represents hydrogen, cyano or formyl or represents alkyl which isoptionally substituted by halogen, cyano, carboxyl, alkoxy, alkenyloxy,alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkoxycarbonyl,alkenyl-oxycarbonyl or alkinyloxycarbonyl, R¹ furthermore representsalkenyl or alkinyl, in each case optionally substituted by halogen, R¹furthermore represents alkylcarbonyl, alkenylcarbonyl, alkinylcarbonyl,alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl, in each caseoptionally substituted by halogen, R¹ furthermore represents cycloalkylor cycloalkylcarbonyl, in each case optionally substituted by halogen,cyano or carboxyl, R² represents hydrogen, cyano or formyl, orrepresents alkyl which is optionally substituted by halogen, cyano,carboxyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio,alkinylthio, alkoxycarbonyl, alkenyloxycarbonyl or alkinyloxycarbonyl,R² furthermore represents alkenyl or alkinyl, in each case optionallysubstituted by halogen, R² furthermore represents alkylcarbonyl,alkenylcarbonyl, alkinylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl oralkinyloxycarbonyl, in each case optionally substituted by halogen, R²furthermore represents cycloalkyl or cycloalkylcarbonyl, in each caseoptionally substituted by halogen, cyano or carboxyl, and Ar representsthe substituted monocyclic or bicyclic aryl or heteroaryl groupingdefined below.

 in which R³ represents hydrogen or halogen, R⁴ represents hydrogen orhalogen, R⁵ represents cyano, carboxyl, chlorocarbonyl, carbamoyl,thiocarbamoyl, hydroxyl or halogen, or represents alkyl, alkoxy oralkoxycarbonyl, in each case optionally substituted by halogen, R⁶represents the following grouping —A¹—A²—A³  in which A¹ represents asingle bond, or represents oxygen, sulfur, —SO—, —SO₂—, —CO— or thegrouping —N—A⁴—, in which A⁴ represents hydrogen, hydroxyl, alkyl,alkenyl, alkinyl, alkoxy, aryl, alkylcarbonyl, arylcarbonyl,alkylsulfonyl or arylsulfonyl, A¹ furthermore represents alkanediyl,alkenediyl, azaalkenediyl, alkanediyl, cycloalkanediyl, cycloalkenediylor phenylene, in each case optionally substituted by halogen, A²represents a single bond, or represents oxygen, sulfur, —SO—, —SO₂—,—CO— or the grouping —N—A⁴—, in which A⁴ represents hydrogen, hydroxyl,alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl, A² furthermorerepresents alkanediyl, alkenediyl, azaalkenediyl, alkinediyl,cycloalkanediyl, cycloalkenediyl or phenylene, in each case optionallysubstituted by halogen, A³ represents hydrogen, with the proviso that inthis case A¹ and/or A² do(es) not represent any single bond, A³furthermore represents hydroxyl, mercapto, amino, cyano, isocyano,thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo,chlorosulfonyl or halogen, or represents alkyl, alkoxy, alkylthio,alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonylor dialkoxy(thio)-phosphoryl, in each case optionally substituted byhalogen or alkoxy, A³ furthermore represents alkenyl, alkenyloxy,alkenylthio, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkinyl,alkinyloxy, alkinylthio, alkynylamino or alkinyloxycarbonyl, in eachcase optionally substituted by halogen A³ furthermore representscycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy,cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl,in each case optionally substituted by halogen, cyano, carboxyl. alkyland/or alkoxy carbonyl, A³ furthermore represents aryl, aryloxy,aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbonyl, in each caseoptionally substituted by nitro, cyano, carboxyl, halogen, alkyl,halogenalkyl, allyloxy, halogenalkyloxy and/or alkoxy-carbonyl, A³furthermore represents in each case optionally completely or partlyhydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl,oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl,pyrimidinyl, triazinyl, pyrazolylalkyl, furylalkyl, thienylalkyl,oxazolylalkyl, isoxazolylalkyl, thiazolylalkyl, pyridinylalkyl,pyrimidinylalkyl, pyrazolylalkoxy or furylalkoxy, or representsperhydropyranylalkoxy or pyridylalkoxy, and R⁷ represents hydrogen orhalogen, or in each case two adjacent radicals—R³ and R⁴, R⁴ and R⁵, R⁵and R⁶ or R⁶ and R⁷—together represent one of the following groupings—Q³—CQ⁴—, —Q³—CQ⁴—Q⁵—, —Q³—C(R⁸,R⁹)—Q⁵—, —C(R⁸,R⁹)—CQ⁴—,—C(R⁸,R⁹)—Q³—CQ⁴—, —Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—, —Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—Q⁵—,—C(R⁸,R⁹)—C(R⁸,R⁹)—CQ⁴—, —Q³—C(R⁸)═C(R⁸)—, —C(R⁸)═C(R⁸)—CQ⁴—,—Q³—C(R⁸,R⁹)—CQ⁴—, —N(R¹⁰)—C(R⁸,R⁹)—CQ⁴—, —C(R⁸)═N—, —Q—CQ⁴—C(R⁸,R⁹)—,—Q³—CQ⁴—N(R¹⁰)—, —Q³—C(R⁸,R⁹)—CQ⁴—N—(R¹⁰)—, —C(R⁸,R⁹)—Q³—CQ⁴—N(R¹⁰)—,—C(R⁸,R⁹)—C(R⁸,R⁹)—N(R¹⁰)—, —C(R⁸,R⁹)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—,—C(R⁸)═C(R⁸)—N(R¹⁰)—, —C(R⁸)═C(R⁸)—CQ⁴—N(R¹⁰)—,—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—N(R¹⁰)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—, —C(R⁸)═N—N(R¹⁰)—,—Q³—CQ⁴—C(R⁸,R⁹)—N(R¹⁰)—, Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—  in which Q³,Q⁴, and Q⁵ are identical or different and in each case represent oxygenor sulfur, R⁸ and R⁹ are identical or different and individuallyrepresent hydrogen, halogen or alkyl or together represent alkanediyl,and R¹⁰ represents hydrogen or hydroxyl, or represents alkyl,alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl which are optionallysubstituted by cyano, halogen, alkoxy, alkyl-carbonyl oralkoxy-carbonyl, or represents alkenyl or alkinyl, in each caseoptionally substituted by halogen, or represents cycloalkyl orcycloalkylalkyl, in each case optionally substituted by halogen oralkyl, or represents alkoxy or alkenyloxy, in each case optionallysubstituted by halogen, or represents arylalkyl or arylalkoxy, in eachcase optionally substituted by cyano, halogen, allyl, halogenoalkyl,alkoxy or halogenoalkoxy, excluding the compounds4-(3,4-dichlorophenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one and4-(4-chloro-3-trifluoromethylphenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one.2. A substitute N-aryl nitrogen-containing heterocyclic compound of thegeneral formula (Ia)

in which Q¹, Q², R¹, R² and Ar have the meanings given in claim
 1. 3. Asubstituted N-aryl nitrogen-containing heterocyclic compound of thegeneral formula (Ib)

in which Q¹, Q², R¹, R² and Ar have the meanings given in claim
 1. 4. Aprocess for the preparation of a substituted N-aryl nitrogen-containingheterocyclic compound of the general formula (I) or of a compound of theformula (Ia) or (Ib) as claimed in claims 1 to 3, which comprises aprocedure in which (a) a (thio)semicarbazide derivative of the generalformula (II)

 in which Q¹, Q², R¹, R² and Ar have the meanings given in claim 1 and Rrepresents alkyl, is subjected to a cyclizing condensation reaction, ifappropriate in the presence of a reaction auxiliary and if appropriatein the presence of a diluent, and thereafter, if appropriate,electrophilic or nucleophilic substitution reactions are carried out inthe customary manner in the context of the definition of thesubstituents, or in wich (b) an aryliminoheterocyclic compound of thegeneral formula (III)

 in which Q¹, Q², R¹, R² and Ar have the abovementioned meanings, — or acompound of the formula (Ia) or (Ib)—above— is isomerized thermally(“pyrolytically”), if appropriate in the presence of a reactionauxiliary and if appropriate in the presence of a diluent.
 5. Asubstituted N-aryl nitrogen-containing heterocyclic compound of thegeneral formula (I), (Ia) or (Ib) as claimed in claims 1 to 3, in whichQ¹ represents oxygen or sulfur, Q² represents oxygen or sulfur, R¹represents hydrogen, cyano or formyl, or represents C₁-C₆-alkyl, in eachcase optionally substituted by fluorine, chlorine, cyano, carboxyl,C₁-C₄-alkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkyloxy, C₁-C₄-alkylthio,C₃-C₄-alkenylthio, C₃-C₄-alkylthio, C₁-C₄-alkoxy carbonyl,C₃-C₄-alkenyloxy-carbonyl or C₃-C₄-alkinyloxy carbonyl, R¹ furthermorerepresents C₃-C₆-alkenyl or C₃-C₆-alkinyl, in each case optionallysubstituted by fluorine or chlorine, R¹ furthermore representsC₁-C₆-alkyl-carbonyl, C₃-C₆-alkenyl-carbonyl, C₃-C₆-alkinylcarbonyl,C₁-C₆-alkoxy-carbonyl, C₃-C₆-alkenyloxy-carbonyl orC₃-C₆-alkinyloxy-carbonyl, in each case optionally substituted byfluorine or chlorine, R¹ furthermore represents C₃-C₆-cycloalkyl orC₃-C₆-cycloalkyl-carbonyl, in each case optionally substituted byfluorine, chlorine, bromine, cyano or carboxyl, R² represents hydrogen,cyano or formyl, or represents C₁-C₆-alkyl, in each case optionallysubstituted by fluorine, chlorine, cyano, carboxyl, C₁-C₄-alkoxy,C₃-C₄-alkenyloxy, C₃-C₄-alkinyloxy, C₁-C₄-alkylthio, C₃-C₄-alkenylthio,C₃-C₄-adylthio, C₁-C₄-alkoxy-carbonyl, C₃-C₄-alkenyloxy-carbonyl orC₃-C₄-alkinyloxy-carbonyl, R² furthermore represents C₃-C₆-alkenyl orC₃-C₆-alkinyl, in each case optionally substituted by fluorine orchlorine, R² furthermore represents C¹-C₆-alkyl-carbonyl,C₃-C₆-alkenyl-carbonyl, C₃-C₆-alkinyl-carbonyl, C₁-C₆-alkoxy-carbonyl,C₃-C₆-alkenyloxy-carbonyl or C₃-C₆-alkinyloxy carbonyl, in each caseoptionally substituted by fluorine or chlorine, R² furthermorerepresents C₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-carbonyl, in each caseoptionally substituted by fluorine, chlorine, bromine, cyano orcarboxyl, and Ar represents the, substituted monocyclic or bicyclic arylor heteroaryl grouping defined below

 in which R³ represents hydrogen, fluorine, chlorine or bromine, R⁴represents hydrogen, fluorine, chlorine or bromine, R⁵ represents cyano,carboxyl, chlorocarbonyl, carbamoyl, thiocarbamoyl, hydroxyl, fluorine,chlorine, bromine or represents alkyl, alkoxy or alkoxycarbonyl havingin each case up to 4 carbon atoms and in each case optionallysubstituted by fluorine and/or chlorine, R⁶ represents the followinggrouping —A¹—A²—A³  in which A¹ represents a single bond, or representsoxygen, sulfur, —SO—, —SO₂—, —CO— or the grouping —NA⁴—, in which A⁴represents hydrogen, hydroxyl, C₁-C₄-alkyl, C₃-C₄-alkenyl,C₃-C₄-alkinyl, C₁-C₄-alkoxy, phenyl, C₁-C₄-alkyl carbonyl,phenyl-carbonyl, C₁-C₄-alkyl-sulfonyl or phenylsulfonyl, A¹ furthermorerepresents C₁-C₆-alkanediyl, C₂-C₆-alkenediyl, C₂-C₆-azaalkenediyl,C₂-C₆-alkenediyl, C₃-C₆-cycloalkanediyl, C₃-C₆-cycloalkenediyl orphenylene, in each case optionally substituted by fluorine, chlorine orbromine, A² represents a single bond, or represents oxygen, sulfur,—SO—, —SO₂—, —CO— or the grouping —N—A⁴—, in which A⁴ representshydrogen, hydroxyl, C₁-C₄-alkyl, C₁-C₄-alkoxy, phenyl,C₁-C₄-alkylsulfonyl or phenylsulfonyl, A² furthermore representsC₁-C₆-alkenediyl, C₂-C₆-alkenediyl, C₂-C₆-azaakenediyl,C₂-C₆-alkinediyl, C₃-C₆-cloallediyl, C₃-C₆-cycloalkenediyl or phenylene,in each case optionally substituted by fluorine, chlorine or bromine, A³represents hydrogen, with the proviso that in this case A¹ and/or A²do(es) not represent a single bond, A³ furthermore represents hydroxyl,mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxyl,carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine orbromine, A³ furthermore represents alkyl, alkoxy, alkylthio,alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonylor dialkoxy(thio)phosphoryl having in each case 1 to 6 carbon atoms inthe alkyl groups and in each case optionally substituted by fluorine,chlorine or C₁-C₄-alkoxy, A³ furthermore represents alkenyl, alkenyloxy,alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkinyl, alkinyloxy,alkinylamino or alkinyloxycarbonyl having in each case 2 to 6 carbonatoms in the alkenyl, alkylidene or alkinyl groups and in each caseoptionally substituted by fluorine or chlorine, A³ furthermorerepresents cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy,cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonylhaving in each case 3 to 6 carbon atoms in the cycloalkyl groups andwhere appropriate 1 to 4 carbon atoms in the alkyl groups and in eachcase optionally substituted by fluorine, chlorine, cyano, carboxyl,C₁-C₄-alkyl and/or C₁-C₄-alkoxy-carbonyl, A³ furthermore representsphenyl, phenyloxy, phenyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy,pentyloxycarbonyl or phenyl-C₁-C₄-alkoxycarbonyl, in each caseoptionally substituted by nitro, cyano, carboxyl, fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkyloxy,C₁-C₄-halogenalkyloxy and/or C₁-C₄-alkoxycarbonyl, A³ furthermorerepresents in each case optionally completely or partly hydrogenatedpyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl,dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl,pyrazolyl-C₁-C₄-alkyl, furyl-C₁-C₄-alkyl, thienyl-C₁-C₄-alkyl,oxalolyl-C₁-C₄-alkyl, isoxazolyl-C₁-C₄-alkyl, thiazolyl-C₁-C₄-alkyl,pyridinyl-C₁-C₄-alkyl, pyridinyl-C₁-C₄-alkyl, pyrazolylmethoxy orfurthermore, or represents perhydropyranylmethoxy or pyridylmethoxy, andR⁷ represents hydrogen, fluorine or chlorine or in each case twoadjacent radicals—R³ and R⁴, R⁴ and R⁵, R⁵ and R⁶ or R⁶ and R⁷—togetherrepresent one of the following groupings —Q³—CQ⁴—, —Q³—CQ⁴—Q⁵—,—Q³—C(R⁸,R⁹)—Q⁵—, —C(R⁸,R⁹)—CQ⁴—, —C(R⁸,R⁹)—Q³—CQ⁴—,—Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—, Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—Q⁵—,—C(R⁸,R⁹)—C(R⁸,R⁹)—CQ⁴—, —Q³—C(R⁸)═C(R⁸)—, —C(R⁸)═C(R⁸)—CQ⁴—,—Q³—C(R⁸,R⁹)—CQ⁴—, —N(R¹⁰)—C(R⁸,R⁹)—CQ⁴—, —C(R⁸)═N—, —Q³—CQ⁴—C(R⁸,R⁹)—,—Q³—CQ⁴—N(R¹⁰)—, —Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—N(R¹⁰)—, —C(R⁸,R⁹)—C(R⁸,R⁹)—,CQ⁴—N(R¹⁰)—, —C(R⁸)═C(R⁸)—N(R¹⁰)—, —C(R⁸)═C(R⁸)—CQ⁴—N(R¹⁰)—, —C(R⁸,R⁹)—,—CQ⁴—N(R¹⁰)—, —C(R⁸,R⁹)—Q³—CQ⁴—N(R¹⁰)—, —C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—,—N(R¹⁰)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—, —C(R⁸)═N—N(R¹⁰)—,—Q³—CQ⁴—C(R⁸,R⁹)—N(R¹⁰)—, Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—,  in whichQ³, Q⁴ and Q⁵ are identical or different and in each case representoxygen or sulfur, R⁸ and R⁹ are identical or different and individuallyrepresent oxygen, fluorine, chlorine, bromine or C₁-C₄-alkyl or togetherrepresent C₂-C₅-alkanediyl, and R¹⁰ represents hydrogen or hydroxyl, orrepresents alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl havingin each case 1 to 6 carbon atoms in the alkyl groups and in each caseoptionally substituted by cyano, fluorine, chlorine, C₁-C₄-alkoxy,C₁-C₄-alkyl carbonyl or C₁-C₄-alkoxy-carbonyl, R¹⁰ furthermorerepresents alkenyl or alkinyl having in each case 2 to 6 carbon atomsand in each case optionally substituted by fluorine, chlorine orbromine, R¹⁰ furthermore represents cycloalkyl or cycloalkylalkyl havingin each case 3 to 6 carbon atoms in the cycloalkyl groups and whereappropriate 1 to 3 atoms in the alkyl group and in each case optionallysubstituted by fluorine, chlorine, bromine or C₁-C₄-alkyl, R₁₀furthermore represents alkoxy or alkenyloxy having in each case up to 6carbon atoms and in each case optionally substituted by fluorene and/orchlorine, and R¹⁰ furthermore represents benzyl or benzyloxy, in eachcase optionally substituted by cyano, fluorene, chlorine, C₁-C₄-alkyl,C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₄-halogenoalkoxy, excluding thecompounds4-(3,4-dichloro-phenyl)-1,2-dimethyl-5-thioxo-1,2,4-tiazolidin-3-one and4-(4-chloro-3-trifluoromethyl-phenyl)-1,2-dimethyl-5-thioxo-1,2,4-triazolidin-3-one.6. A substituted N-aryl nitrogen-containing heterocyclic compound of thegeneral formula (I), (Ia) or (Ib) as claimed in claims 1 to 3, in whichQ¹ represents oxygen or sulfur, Q² represents oxygen or sulfur, R¹represents hydrogen, cyano or formyl, or represents methyl, ethyl, n- ori-propyl or n-, i-, s- or t-butyl, in each case optionally substitutedby fluorine, chlorine, cyano, carboxyl, methoxy or ethoxy, R¹furthermore represents propenyl, butenyl, propinyl or butinyl, in eachcase optionally substituted by fluorine or chlorine, R¹ furthermorerepresents acetyl, propionyl, methoxycarbonyl or ethoxy-carbonyl, ineach case optionally substituted by fluorine or chlorine, R¹ furthermorerepresents cyclopropyl which is optionally substituted by fluorine orchlorine, R² represents hydrogen, cyano or formyl, or represents methyl,ethyl, n- or i-propyl or n-, i-, s- or t-butyl, in each case optionallysubstituted by fluorine, chlorine, cyano, carboxyl, methoxy or ethoxy,R² furthermore represents propenyl, butenyl, propinyl or butinyl, ineach case optionally substituted by fluorine or chlorine, R² furthermorerepresents acetyl, propionyl, methoxycarbonyl or ethoxy-carbonyl, ineach case optionally substituted by fluorine or chlorine, R² furthermorerepresents cyclopropyl which is optionally substituted by fluorine orchlorine, and Ar represents the substituted monocyclic or bicyclic arylor heteroaryl grouping defined below

 in which R³ represents hydrogen, fluorine or chlorine, R⁴ representshydrogen, fluorine or chlorine, R⁵ represents cyano, thiocarbamoyl,chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy ortrifluoro-methoxy, R⁶ represents the following grouping —A¹—A²—A³  inwhich A¹ represents a single bond, or represents oxygen, sulfur, —SO—,—SO₂—, —CO—0 or the grouping —N—A⁴—, in which A⁴ represents hydrogen,hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- ori-propoxy, methylsulfonyl or ethylsulfonyl, A¹ furthermore representsmethylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl,propane-1,2-diyl, propane-1,3-diyl, ethene-1,2,-diyl, propane-1,2-diyl,propane-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl,A² represents a single bond, or represents oxygen, sulfur, —SO—, —SO₂—,—CO— or the grouping —N—A⁴—, in which A⁴ represents oxygen, hydroxyl,methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,A² furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl,propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl,propane-1,2-diyl, propane-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl orpropine-1,3-diyl, A³ represents hydrogen, with the proviso that in thiscase A¹ and/or A² do(es) not represent a single bond, A³ furthermorerepresents hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulfo,fluorine, chlorine or bromine, A³ furthermore represents methyl, ethyl,n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy,ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- ort-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- ort-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl,methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino,dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl,dipropoxyphosphoryl or diisopropoxyphosphoryl, in each case optionallysubstituted by fluorine, chlorine, methoxy or ethoxy, A³ furthermorerepresents propenyl, butenyl, propenyloxy, butenyloxy, propenylamino,butenylamino, propylidenamino, butylidenamino, propenyloxycarbonyl,butenyloxycarbonyl, propinyl, butinyl, propinyloxy, butinyloxy,propinylamino, butinylamino, propinyloxycarbonyl or butinyloxycarbonyl,in each case optionally substituted by fluorine or chlorine, A³furthermore represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy,cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidenamino,cyclobexylidenamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl,cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, in each caseoptionally substituted by fluorine, chlorine, cyano, carboxyl, methyl,ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, A³ furthermorerepresents phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy,phenyloxycarbonyl or benzyloxycarbonyl, in each case optionallysubstituted by nitro, cyano, carboxyl, fluorine, chlorine, bromine,methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- ori-propoxy, difluoromethoxy, trifluoromethoxy, methoxy-carbonyl and/orethoxycarbonyl, A³ furthermore represents in each case optionallycompletely or partly hydrogenated pyrrolyl, pyrazolyl, imidazolyl,triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl,isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl,triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl,isoxazolylmethyl, thiazolylmethyl, pyridinylmethyl, pyrimidinylmethyl,pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, R⁷ representshydrogen, fluorine or chlorine, or in each case two adjacent radicals—R³and R⁴, R⁴ and R⁵, R⁵ and R⁶ or R⁶ and R⁷—together represent one of thefollowing groupings —Q³—CQ⁴—, —Q³—CQ⁴—Q⁵—, —Q³—C(R⁸,R⁹)—Q⁵—,—C(R⁸,R⁹)—CQ⁴—, —C(R⁸,R⁹)—Q³—CQ⁴—, —Q³—C(R⁸,R⁹)—C(R⁸,R⁹),—Q—C(R⁸,R⁹)—C(R⁸,R⁹)—Q⁵—, —C(R⁸,R⁹)—C(R⁸,R⁹)—CQ⁴—, —Q³—(R⁸)═C(R⁸)—,—C(R⁸)═C(R⁸)—CQ⁴—, —Q³—C(R⁸,R⁹)—CQ⁴—, —N(R¹⁰)—C(R⁸,R⁹)—CQ⁴—, —C(R⁸)═N—,—Q³—CQ⁴—C(R⁸,R⁹)—, —Q³—CQ⁴—N(R¹⁰)—, —Q³—CR(R⁸,R⁹)—CQ⁴—N—(R¹⁰)—,—C(R⁸,R⁹)—Q³—CQ⁴—N(R¹⁰)—, —C(R⁸,R⁹)—C(R⁸,R⁹)—N(R¹⁰)—,—C(R⁸,R⁹)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—, —C(R⁸)═C(R⁸)—N(R¹⁰)—,—C(R⁸)═C(R⁸)—CQ⁴—N(R¹⁰)—, —C(R⁸)═C(R⁸)—N(R¹⁰)—,—C(R⁸)═C(R⁸)—CQ⁴—N(R¹⁰)—, —C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—,—N(R¹⁰)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—, —C(R⁸)═N—N(R¹⁰)—,—Q³—CQ⁴—C(R⁸,R⁹)—N(R¹⁰)—, Q³—C(R⁸,R⁹)—C(R⁸,R⁹)—CQ⁴—N(R¹⁰)—,  in whichQ³, Q⁴ and Q⁵ are identical or different and in each case representoxygen or sulfur, R⁸ and R⁹ are identical or different and individuallyrepresent hydrogen, fluorine, chlorine, methyl or ethyl or togetherrepresent ethane-1,2-diyl(dimethylene), and R¹⁰ represents hydrogen orhydroxyl, or represents methyl, ethyl, n- or i-propyl or n-, i-, s- ort-butyl which are optionally substituted by cyano, fluorine, chlorine,methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl,R¹⁰ furthermore represents propenyl, butenyl, propinyl or butinyl, ineach case optionally substituted by fluorine, chlorine or bromine, R¹⁰furthermore represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, in each case optionally substituted by fluorine,chlorine, bromine, methyl or ethyl, R¹⁰ furthermore represents methoxy,ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy or butenyloxy,in each case optionally substituted by fluorine and/or chlorine, and R¹⁰furthermore represents benzyl or benzyloxy, in each case optionallysubstituted by cyano, fluorine, chlorine, methyl, ethyl,trifluoromethyl, methoxy, ethoxy, difluoromethyl or trifluoromethoxy,excluding the compounds4-(3,4-dichloro-phenyl)-1,2-dimethyl-5-thioxo-1,2,-triazolidin-3-one and4-(4-chloro-3-trifluoromethyl-phenyl)1,2-diethyl-5-thioxo-1,2,4-triazolidin-3-one.7. A herbicidal composition which has a content of at least one N-arylnitrogen-containing heterocyclic compound of the general formula (I),(Ia) or (Ib) as claimed in claims 1 to
 6. 8. A method of combatingundesirable plants which comprises allowing an N-arylnitrogen-containing heterocyclic compound of the general formula (I),(Ia) or (Ib) as claimed in claims 1 to 6 to act on undesirable plantsand/or their environment.
 9. The use of an N-aryl nitrogen-containingheterocyclic compound of the general formula (I), (Ia) or (Ib) asclaimed in claims 1 to 6 for combating undesirable plants.
 10. A processfor the preparation of a herbicidal composition, which comprises mixingan N-aryl nitrogen-containing heterocyclic compound of the generalformula (I), (Ia) or (Ib) as claimed in claims 1 to 6 with extendersand/or surface-active substances.